Skip to main content
SpringerLink
Log in

Metalation of Indole

  • Chapter
  • First Online:
Heterocyclic Scaffolds II:

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 26))

Abstract

Metalation reactions involving indoles (and indolines) is reviewed (through 2009). The most common mode of metalation is lithiation. Other metals that have been used, either through direct metalation of indole or through transmetalation, include magnesium, zinc, tin, and boron. This monograph is divided into three sections: metalation directed by a nitrogen functionality, directed ortho metalation by substituents not located at nitrogen, and halogen–metal exchange. All of the sections are organized by the location of the metalation event. The review will have a primary focus on the seminal papers that contributed to the development of metalation reactions and a secondary focus on applications of metalation reactions used in the synthesis of complex indoles including indole natural products.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 429.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 549.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 549.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Beak P, Snieckus V (1982) Acc Chem Res 15:306

    Article  CAS  Google Scholar 

  2. Snieckus V (1990) Chem Rev 90:879

    Article  CAS  Google Scholar 

  3. Anctil EJG, Snieckus V (2002) J Organomet Chem 653:150

    Article  CAS  Google Scholar 

  4. Chinchilla R, Nájera C, Yus M (2004) Chem Rev 104:2667

    Article  CAS  Google Scholar 

  5. Rewcastle GW, Katritzky AR (1993) Adv Heterocycl Chem 56:155

    Article  CAS  Google Scholar 

  6. Gilman H, Kirby RH (1936) J Org Chem 1:146

    Article  CAS  Google Scholar 

  7. Shirley DA, Roussel PA (1953) J Am Chem Soc 75:375

    Article  CAS  Google Scholar 

  8. Gschwend HW, Rodriguez HR (1979) Org React (NY) 26:1

    CAS  Google Scholar 

  9. Sundberg RJ, Russell HF (1973) J Org Chem 38:3324

    Article  CAS  Google Scholar 

  10. Sundberg RJ, Parton RL (1976) J Org Chem 41:163

    Article  CAS  Google Scholar 

  11. Hasan I, Marinelli ER, Lin LCC, Fowler FW, Levy AB (1981) J Org Chem 46:157

    Article  CAS  Google Scholar 

  12. Katritzky A, Akutagawa K (1985) Tetrahedron Lett 26:5935

    Article  CAS  Google Scholar 

  13. Katritzky AR, Akutagawa K (1986) J Am Chem Soc 108:6808

    Article  CAS  Google Scholar 

  14. Saulnier MG, Gribble GW (1982) J Org Chem 47:757

    Article  CAS  Google Scholar 

  15. Moyer MP, Shiurba JF, Rapoport H (1986) J Org Chem 51:5106

    Article  CAS  Google Scholar 

  16. Iwao M (1993) Heterocycles 36:29

    Article  CAS  Google Scholar 

  17. Matsuzono M, Fukuda T, Iwao M (2001) Tetrahedron Lett 42:7621

    Article  CAS  Google Scholar 

  18. Fukuda T, Mine Y, Iwao M (2001) Tetrahedron 57:975

    Article  CAS  Google Scholar 

  19. Hartung CG, Fecher A, Chapell B, Snieckus V (2003) Org Lett 5:1899

    Article  CAS  Google Scholar 

  20. Ziegler FE, Spitzner EB (1970) J Am Chem Soc 92:3492

    Article  CAS  Google Scholar 

  21. Ziegler FE, Spitzner EB (1973) J Am Chem Soc 95:7146

    Article  CAS  Google Scholar 

  22. Besserlievre R, Thal C, Husson HP, Potier P (1975) J Chem Soc, Chem Commun 90

    Google Scholar 

  23. Watanabe M, Snieckus V (1980) J Am Chem Soc 102:1457

    Article  CAS  Google Scholar 

  24. Kano S, Sugino E, Shibuya S, Hibino S (1981) J Org Chem 46:2979

    Article  CAS  Google Scholar 

  25. Taylor DA, Joule JA (1979) J Chem Soc, Chem Commun 642

    Google Scholar 

  26. Saulnier MG, Gribble GW (1982) J Org Chem 47:2810

    Article  CAS  Google Scholar 

  27. Gribble GW, Saulnier MG, Sibi MP, Obaza-Nutaitis JA (1984) J Org Chem 49:4518

    Article  CAS  Google Scholar 

  28. Gribble GW (1991) Synlett 289

    Google Scholar 

  29. Gribble GW, Keavy DJ, Davis DA, Saulnier MG, Pelcman B, Barden TC, Sibi MP, Olson ER, BelBruno JJ (1992) J Org Chem 57:5878

    Article  CAS  Google Scholar 

  30. Gribble GW, Saulnier MG, Obaza-Nutaitis JA, Ketcha DM (1992) J Org Chem 57:5891

    Article  CAS  Google Scholar 

  31. Gribble GW, Barden TC (1985) J Org Chem 50:5900

    Article  CAS  Google Scholar 

  32. Gribble GW, Barden TC, Johnson DA (1988) Tetrahedron 44:3195

    Article  CAS  Google Scholar 

  33. Iwao M, Ishibashi F (1997) Tetrahedron 53:51

    Article  CAS  Google Scholar 

  34. Shinohara H, Fukuda T, Iwao M (1999) Tetrahedron 55:10989

    Article  CAS  Google Scholar 

  35. Ishikura M, Terashima M (1989) J Chem Soc, Chem Commun 135

    Google Scholar 

  36. Ishikura M, Matsuzaki Y, Agata I (1997) Heterocycles 45:2309

    Article  CAS  Google Scholar 

  37. Ishikura M, Agata I, Katagiri N (1999) J Heterocycl Chem 36:873

    Article  CAS  Google Scholar 

  38. Ishikura M, Terashima M (1990) Heterocycles 31:2091

    Article  CAS  Google Scholar 

  39. Ishikura M, Terashima M, Okamura K, Date T (1991) J Chem Soc, Chem Commun 1219

    Google Scholar 

  40. Ishikura M, Terashima M (1992) Tetrahedron Lett 33:6849

    Article  CAS  Google Scholar 

  41. Ishikura M, Terashima M (1994) J Org Chem 59:2634

    Article  CAS  Google Scholar 

  42. Ishikura M, Ida W, Yanada K (2006) Tetrahedron 62:1015

    Article  CAS  Google Scholar 

  43. Ishikura M, Uemura R, Yamada K, Yanada R (2006) Heterocycles 68:2349

    Article  CAS  Google Scholar 

  44. Caixach J, Capell R, Galvez C, Gonzalez A, Roca N (1979) J Heterocycl Chem 16:1631

    Article  CAS  Google Scholar 

  45. Fraser RR, Mansour TS, Savard S (1985) Can J Chem 63:3505

    Article  CAS  Google Scholar 

  46. Conway B, Hevia E, Kennedy AR, Mulvey RE (2007) Chem Commun 2864

    Google Scholar 

  47. Kebrle J, Rossi A, Hoffmann K (1959) Helv Chim Acta 42:907

    Article  CAS  Google Scholar 

  48. Akgün E, Tunali M, Erdönmez G (1989) J Heterocycl Chem 26:1869

    Article  Google Scholar 

  49. Ganellin CR, Ridley HF (1969) J Chem Soc 1537

    Google Scholar 

  50. Sundberg RJ, Smith FX (1975) J Org Chem 40:2613

    Article  CAS  Google Scholar 

  51. Bergman J, Eklund N (1980) Tetrahedron 36:1439

    Article  CAS  Google Scholar 

  52. Clerici F, Gelmi ML, Rossi LM (1987) Synthesis 1025

    Google Scholar 

  53. Hlasta D, Court J (1989) Tetrahedron Lett 30:1773

    Article  CAS  Google Scholar 

  54. Yokoyama Y, Toyoshima H, Shimizu M, Togo H (1997) J Chem Soc, Perkin Trans 1 29

    Google Scholar 

  55. Benincori T, Sannicoló F, Trimarco L, Bonati L, Grandi S, Pitea D, Gatti C (1998) J Phys Org Chem 11:455

    Article  CAS  Google Scholar 

  56. Sanin AV, Nenajdenko VG, Smolko KI, Denisenko DI, Balenkova ES (1998) Synthesis 842

    Google Scholar 

  57. Rewcastle G, Janosik T, Bergman J (2001) Tetrahedron 57:7185

    Article  CAS  Google Scholar 

  58. Rigolet S, McCort I, Le Merrer Y (2002) Tetrahedron Lett 43:8129

    Article  CAS  Google Scholar 

  59. Cutri S, Diez A, Bonin M, Micouin L, Husson HP (2005) Org Lett 7:1911

    Article  CAS  Google Scholar 

  60. Qi T, Qiu W, Liu Y, Zhang H, Gao X, Liu Y, Lu K, Du C, Yu G, Zhu D (2008) J Org Chem 73:4638

    Article  CAS  Google Scholar 

  61. Minato A, Tamao K, Hayashi T, Suzuki K, Kumada M (1981) Tetrahedron Lett 22:5319

    Article  CAS  Google Scholar 

  62. Labadie SS, Teng E (1994) J Org Chem 59:4250

    Article  CAS  Google Scholar 

  63. Liu F, Liebeskind LS (1998) J Org Chem 63:2835

    Article  CAS  Google Scholar 

  64. Sun L, Liebeskind LS (1996) J Am Chem Soc 118:12473

    Article  CAS  Google Scholar 

  65. Fargeas V, Bavresse F, Mathieu D, Beaudet I, Charrue P, Lebret B, Piteau M, Quintard J-P (2003) Eur J Org Chem 1711

    Google Scholar 

  66. Arnswald M, Neumann WP (1993) J Org Chem 58:7022

    Article  CAS  Google Scholar 

  67. Hodson HF, Madge DJ, Widdowson DA (1992) Synlett 831

    Google Scholar 

  68. Levy AB (1978) J Org Chem 43:4684

    Article  CAS  Google Scholar 

  69. Ishikura M, Kamada M, Oda I, Ohta T, Terashima M (1987) J Heterocycl Chem 24:377

    Article  Google Scholar 

  70. Ishikura M, Takahashi N, Yamada K, Yanada R (2006) Tetrahedron 62:11580

    Article  CAS  Google Scholar 

  71. Levy AB (1979) Tetrahedron Lett 21:4021

    Article  Google Scholar 

  72. Ukai K, Aoki M, Takaya J, Iwasawa N (2006) J Am Chem Soc 128:8706

    Article  CAS  Google Scholar 

  73. Nicolaou KC, Dalby SM, Majumder U (2008) J Am Chem Soc 130:14942

    Article  CAS  Google Scholar 

  74. Albrecht K, Kaiser V, Boese R, Adams J, Kaufmann DE (2000) J Chem Soc, Perkin Trans 2:2153

    Google Scholar 

  75. Herz H-G, Queiroz MJRP, Maas G (1999) Synthesis 1013

    Google Scholar 

  76. Bisagni E, Hung NC, Lhoste JM (1983) Tetrahedron 39:1777

    Article  CAS  Google Scholar 

  77. Comins D, Killpack M (1989) Tetrahedron Lett 30:4337

    Article  CAS  Google Scholar 

  78. Adam W, Takayama K (1980) J Org Chem 45:447

    Article  CAS  Google Scholar 

  79. Graham SL, Hoffman JM, Gautheron P, Michelson SR, Scholz TH, Schwam H, Shepard KL, Smith AM, Smith RL, Sondey JM, Sugrue MF (1990) J Med Chem 33:749

    Article  CAS  Google Scholar 

  80. Gilman H, Langham W, Jacoby AL (1939) J Am Chem Soc 61:106

    Article  CAS  Google Scholar 

  81. Familoni OB (2002) Synlett 1181

    Google Scholar 

  82. Mahboobi S, Uecker A, Sellmer A, Cénac C, Höcher H, Pongratz H, Eichhorn E, Hufsky H, Trümpler A, Sicker M, Heidel F, Fischer T, Stocking C, Elz S, Böhmer F-D, Dove S (2006) J Med Chem 49:3101

    Article  CAS  Google Scholar 

  83. Wahlstrom N, Stensland B, Bergman J (2004) Synthesis 1187

    Google Scholar 

  84. Amat M, Llor N, Pshenichnyi G, Bosch J (2002) Arkivoc 73

    Google Scholar 

  85. Mahboobi S, Pongratz H, Hufsky H, Hockemeyer J, Frieser M, Lyseenko A, Paper DH, Bürgermeister J, Böhmer F-D, Fiebig H-H, Burger AM, Baasner S, Beckers T (2001) J Med Chem 44:4535

    Article  CAS  Google Scholar 

  86. Dormoy J, Heymes A (1993) Tetrahedron 49:2885

    Article  CAS  Google Scholar 

  87. Ruckdeschel JC, Modi SP, El-Hamouly W, Portuese E, Archer S (1992) J Med Chem 35:4854

    Article  CAS  Google Scholar 

  88. Praly-Deprez I, Rivalle C, Huel C, Belehradek J, Paoletti C, Bisagni E (1991) J Chem Soc, Perkin Trans 1:3165

    Google Scholar 

  89. Gribble GW, Fletcher GL, Ketcha DM, Rajopadhye M (1989) J Org Chem 54:3264

    Article  CAS  Google Scholar 

  90. Modi SP, Zayed A-H, Archer S (1989) J Org Chem 54:3084

    Article  CAS  Google Scholar 

  91. Jacquemard U, Dias N, Lansiaux A, Bailly C, Logé C, Robert J-M, Lozach O, Meijer L, Mérour J-Y, Routier S (2008) Bioorg Med Chem 16:4932

    Article  CAS  Google Scholar 

  92. Mahboobi S, Uecker A, Cénac C, Sellmer A, Eichhorn E, Elz S, Böhmer F-D, Dove S (2007) Bioorg Med Chem 15:2187

    Article  CAS  Google Scholar 

  93. Smart BP, Oslund RC, Walsh LA, Gelb MH (2006) J Med Chem 49:2858

    Article  CAS  Google Scholar 

  94. Mahboobi S, Teller S, Pongratz H, Hufsky H, Sellmer A, Botzki A, Kassack MU, Dove S, Böhmer F-D (2002) J Med Chem 45:1002

    Article  CAS  Google Scholar 

  95. Utsunomiya I, Muratake H, Natsume M (1995) Chem Pharm Bull 43:37

    Article  CAS  Google Scholar 

  96. Wu J, Sanyal S, Lu Z, Senanayake CH (2009) Tetrahedron Lett 50:5667

    Article  CAS  Google Scholar 

  97. Komoriya S, Kobayashi S, Osanai K, Yoshino T, Nagata T, Haginoya N, Nakamoto Y, Mochizuki A, Nagahara T, Suzuki M, Shimada T, Watanabe K, Isobe Y, Furugoori T (2006) Bioorg Med Chem 14:1309

    Article  CAS  Google Scholar 

  98. Komoriya S, Haginoya N, Kobayashi S, Nagata T, Mochizuki A, Suzuki M, Yoshino T, Horino H, Nagahara T, Suzuki M, Isobe Y, Furugoori T (2005) Bioorg Med Chem 13:3927

    Article  CAS  Google Scholar 

  99. Kuethe JT, Wong A, Davies IW (2003) Org Lett 5:3721

    Article  CAS  Google Scholar 

  100. Iwanowicz EJ, Lau WF, Lin J, Roberts DGM, Seiler SM (1996) Bioorg Med Chem Lett 6:1339

    Article  CAS  Google Scholar 

  101. Sundberg RJ, Broome R, Walters CP, Schnur D (1981) J Heterocycl Chem 18:807

    Article  CAS  Google Scholar 

  102. Sakamoto T, Kondo Y, Takazawa N, Yamanaka H (1996) J Chem Soc, Perkin Trans 1:1927

    Google Scholar 

  103. Naka H, Akagi Y, Yamada K, Imahori T, Kasahara T, Kondo Y (2007) Eur J Org Chem 4635

    Google Scholar 

  104. Grethe G, Lee HL, Uskokovic MR (1976) Helv Chim Acta 59:2268

    Article  CAS  Google Scholar 

  105. Cooper MM, Hignett GJ, Joule JA (1981) J Chem Soc, Perkin Trans 1:3008

    Google Scholar 

  106. Kano S, Sugino E, Hibino S (1980) J Chem Soc, Chem Commun 1241

    Google Scholar 

  107. Pelkey ET, Chang L, Gribble GW (1996) Chem Commun 1909

    Google Scholar 

  108. Gribble G, Pelkey E, Simon W, Trujillo H (2000) Tetrahedron 56:10133

    Article  CAS  Google Scholar 

  109. Jiang J, Gribble GW (2002) Synth Commun 32:2035

    Article  CAS  Google Scholar 

  110. Ketcha DM, Gribble GW (1985) J Org Chem 50:5451

    Article  CAS  Google Scholar 

  111. Roy S, Gribble GW (2005) Tetrahedron Lett 46:1325

    Article  CAS  Google Scholar 

  112. Ketcha DM, Lieurance BA, Homan DFJ, Gribble GW (1989) J Org Chem 54:4350

    Article  CAS  Google Scholar 

  113. Rubiralta M, Casamitjana N, Grierson D, Husson H (1988) Tetrahedron 44:443

    Article  CAS  Google Scholar 

  114. Bergman J, Pelcman B (1988) Tetrahedron 44:5215

    Article  CAS  Google Scholar 

  115. Sundberg RJ, Bloom JD (1980) J Org Chem 45:3382

    Article  CAS  Google Scholar 

  116. Sundberg RJ, Bloom JD (1978) Tetrahedron Lett 20:5157

    Article  Google Scholar 

  117. Gagnon D, Spino C (2009) J Org Chem 74:6035

    Article  CAS  Google Scholar 

  118. Jiang J, Gribble GW (2002) Tetrahedron Lett 43:4115

    Article  CAS  Google Scholar 

  119. Noguchi-Yachide T, Tetsuhashi M, Aoyama H, Hashimoto Y (2009) Chem Pharm Bull 57:536

    Article  CAS  Google Scholar 

  120. Sundberg RJ, Rearick DE, Russell HF (1977) J Pharm Sci 66:263

    Article  CAS  Google Scholar 

  121. Kutney JP, Noda M, Lewis NG, Monteiro B, Mostowicz D, Worth BR (1982) Can J Chem 60:2426

    Article  CAS  Google Scholar 

  122. Kano S, Sugino E, Hibino S (1982) Heterocycles 19:1673

    Article  CAS  Google Scholar 

  123. Berry JM, Bradshaw TD, Fichtner I, Ren R, Schwalbe CH, Wells G, Chew E-H, Stevens MFG, Westwell AD (2005) J Med Chem 48:639

    Article  CAS  Google Scholar 

  124. Fraser HL, Gribble GW (2001) Can J Chem 79:1515

    Article  CAS  Google Scholar 

  125. Hibino S, Sugino E, Kuwada T, Ogura N, Sato K, Choshi T (1992) J Org Chem 57:5917

    Article  CAS  Google Scholar 

  126. Cheng L, Liu L, Sui Y, Wang D, Chen Y (2007) Tetrahedron Asymmetry 18:1833

    Article  CAS  Google Scholar 

  127. Arai Y, Kasai M, Masaki Y (2004) Chem Pharm Bull 52:733

    Article  CAS  Google Scholar 

  128. Aboutayab K, Caddick S, Jenkins K, Joshi S, Khan S (1996) Tetrahedron 52:11329

    Article  CAS  Google Scholar 

  129. Matsuda S, Henry AA, Schultz PG, Romesberg FE (2003) J Am Chem Soc 125:6134

    Article  CAS  Google Scholar 

  130. Guianvarc'h D, Fourrey JL, Tran Huu Dau ME, Guérineau V, Benhida R (2002) J Org Chem 67:3724

    Article  CAS  Google Scholar 

  131. Street JD, Harris M, Bishop DI, Heatley F, Beddoes RL, Mills OS, Joule JA (1987) J Chem Soc, Perkin Trans 1:1599

    Google Scholar 

  132. Aygün A, Pindur U (2000) Synlett 1757

    Google Scholar 

  133. Kano S, Sugino E, Shibuya S, Hibino S (1981) J Org Chem 46:3856

    Article  CAS  Google Scholar 

  134. Lachance N, Chan WY (2003) J Heterocycl Chem 40:289

    Article  CAS  Google Scholar 

  135. Utsunomiya I, Fuji M, Sato T, Natsume M (1993) Chem Pharm Bull 41:854

    Article  CAS  Google Scholar 

  136. Magnus P, Thurston LS (1991) J Org Chem 56:1166

    Article  CAS  Google Scholar 

  137. Lefoix M, Daillant JP, Routier S, Merour JY, Gillaizeau I, Coudert G (2005) Synthesis 3581

    Google Scholar 

  138. Bourderioux A, Kassis P, Mérour Y, Routier S (2008) Tetrahedron 64:11012

    Article  CAS  Google Scholar 

  139. Pelkey ET, Barden TC, Gribble GW (1999) Tetrahedron Lett 40:7615

    Article  CAS  Google Scholar 

  140. Padwa A, Lynch SM, Mejía-Oneto J, Zhang H (2005) J Org Chem 70:2206

    Article  CAS  Google Scholar 

  141. Danieli B, Lesma G, Martinelli M, Passarella D, Peretto I, Silvani A (1998) Tetrahedron 54:14081

    Article  CAS  Google Scholar 

  142. Ayats C, Soley R, Albericio F, Álvarez M (2009) Org Biomol Chem 7:860

    Article  CAS  Google Scholar 

  143. Soley R, Albericio F, Álvarez M (2007) Synthesis 1559

    Google Scholar 

  144. Hodson HF, Madge DJ, Slawin ANZ, Widdowson DA, Williams DJ (1994) Tetrahedron 50:1899

    Article  CAS  Google Scholar 

  145. Brenner M, Mayer G, Terpin A, Steglich W (1997) Chem Eur J 3:70

    Article  CAS  Google Scholar 

  146. Bennasar M-L, Zulaica E, Solé D, Roca T, García-Díaz D, Alonso S (2009) J Org Chem 74:8359

    Article  CAS  Google Scholar 

  147. Bennasar M-L, Zulaica E, Solé D, Alonso S (2009) Chem Commun 3372

    Google Scholar 

  148. Güller R, Dobler M, Borschberg H-J (1991) Helv Chim Acta 74:1636

    Article  Google Scholar 

  149. Amat M, Hadida S, Bosch J (1993) Tetrahedron Lett 34:5005

    Article  CAS  Google Scholar 

  150. Amat M, Hadida S, Pshenichnyi G, Bosch J (1997) J Org Chem 62:3158

    Article  CAS  Google Scholar 

  151. Amat M, Hadida S, Sathyanarayana S, Bosch J (1996) Tetrahedron Lett 37:3071

    Article  CAS  Google Scholar 

  152. Knapp DM, Gillis EP, Burke MD (2009) J Am Chem Soc 131:6961

    Article  CAS  Google Scholar 

  153. Caddick S, Joshi S (1992) Synlett 805

    Google Scholar 

  154. Cooper MM, Lovell JM, Joule JA (1996) Tetrahedron Lett 37:4283

    Article  CAS  Google Scholar 

  155. Cooper MM, Hignett GJ, Newton RF, Joule JA, Harris M, Hinchley JD (1977) J Chem Soc, Chem Commun 432

    Google Scholar 

  156. Beal MG, Ashcroft WR, Cooper MM, Joule JA (1982) J Chem Soc, Perkin Trans 1:435

    Google Scholar 

  157. Passarella D, Giardini A, Martinelli M, Silvani A (2001) J Chem Soc, Perkin Trans 1:127

    Google Scholar 

  158. Danieli B, Lesma G, Luzzani M, Passarella D, Silvani A (1996) Tetrahedron 52:11291

    Article  CAS  Google Scholar 

  159. Conway SC, Gribble GW (1992) Heterocycles 34:2095

    Article  CAS  Google Scholar 

  160. Wagger J, Svete J, Stanovnik B (2008) Synthesis 1436

    Google Scholar 

  161. de la Torre MC, García I, Sierra MA (2005) Chem Eur J 11:3659

    Article  CAS  Google Scholar 

  162. Marino JP, Bogdan S, Kimura K (1992) J Am Chem Soc 114:5566

    Article  CAS  Google Scholar 

  163. Sauer G, Schrôter B, Künzer H (1988) Tetrahedron Lett 29:6429

    Article  CAS  Google Scholar 

  164. Rubiralta M, Diez A, Reig I, Castells J (1990) Heterocycles 31:173

    Article  CAS  Google Scholar 

  165. Hughes TV, Cava MP (1999) J Org Chem 64:313

    Article  CAS  Google Scholar 

  166. Manabe S, Marui Y, Ito Y (2003) Chem Eur J 9:1435

    Article  Google Scholar 

  167. Manabe S, Ito Y (1999) J Am Chem Soc 121:9754

    Article  CAS  Google Scholar 

  168. Joseph B, Alagille D, Rousseau C, Mérour J (1999) Tetrahedron 55:4341

    Article  CAS  Google Scholar 

  169. Nishiura M, Ueda I, Yamamura K (2007) Heterocycles 74:951

    Article  CAS  Google Scholar 

  170. Kusurkar R, Goswami S (2004) Tetrahedron 60:5315

    Article  CAS  Google Scholar 

  171. Kusurkar R, Goswami S, Vyas S (2003) Tetrahedron Lett 44:4761

    Article  CAS  Google Scholar 

  172. Bernardo PH, Chai CLL, Heath GA, Mahon PJ, Smith GD, Waring P, Wilkes BA (2004) J Med Chem 47:4958

    Article  CAS  Google Scholar 

  173. Saulnier MG, Gribble GW (1983) J Org Chem 48:2690

    Article  CAS  Google Scholar 

  174. Marino JP, Kim M-W, Lawrence R (1989) J Org Chem 54:1782

    Article  CAS  Google Scholar 

  175. Denison S, Hilton ST (2004) Synlett 2806

    Google Scholar 

  176. Gribble GW, Jiang J, Liu Y (2002) J Org Chem 67:1001

    Article  CAS  Google Scholar 

  177. Gribble GW, Saulnier MG (1984) J Chem Soc, Chem Commun 168

    Google Scholar 

  178. Saulnier M, Gribble G (1983) Tetrahedron Lett 24:5435

    Article  CAS  Google Scholar 

  179. Jiang J, Gribble G (2002) Org Prep Proced Int 34:543

    Article  Google Scholar 

  180. Gribble GW, Saulnier MG, Pelkey ET, Kishbaugh TLS, Liu YB, Jiang J, Trujillo HA, Keavy DJ, Davis DA, Conway SC, Switzer FL, Roy S, Silva RA, Obaza-Nutaitis JA, Sibi MP, Moskalev NV, Barden TC, Chang L, Habeski WM, Pelcman B, Sponholtz WR, Chau RW, Allison BD, Garaas SD, Sinha MS, McGowan MA, Reese MR, Harpp KS (2005) Curr Org Chem 9:1493

    Article  CAS  Google Scholar 

  181. Shirani H, Janosik T (2007) J Org Chem 72:8984

    Article  CAS  Google Scholar 

  182. Shirani H, Bergman J, Janosik T (2009) Tetrahedron 65:8350

    Article  CAS  Google Scholar 

  183. Liu Y, Gribble GW (2000) Tetrahedron Lett 41:8717

    Article  CAS  Google Scholar 

  184. Gribble GW, Allison BD, Conway SC, Saulnier MG (1992) Org Prep Proced Int 24:649

    Article  CAS  Google Scholar 

  185. Abbiati G, Canevari V, Rossi E, Ruggeri A (2005) Synth Commun 35:1845

    Article  CAS  Google Scholar 

  186. Davis DA, Gribble GW (1992) Heterocycles 34:1613

    Article  CAS  Google Scholar 

  187. Beevers RE, Buckley GM, Davies N, Fraser JL, Galvin FC, Hannah DR, Haughan AF, Jenkins K, Mack SR, Pitt WR, Ratcliffe AJ, Richard MD, Sabin V, Sharpe A, Williams SC (2006) Bioorg Med Chem Lett 16:2535

    Article  CAS  Google Scholar 

  188. Janosik T, Lipson A, Gribble G (2004) Org Prep Proced Int 36:289

    Article  CAS  Google Scholar 

  189. Abbiati G, Beccalli EM, Marchesini A, Rossi E (2001) Synthesis 2477

    Google Scholar 

  190. Desarbre E, Coudret S, Meheust C, Mérour J-Y (1997) Tetrahedron 53:3637

    Article  CAS  Google Scholar 

  191. Mouaddib A, Joseph B, Hasnaoui A, Mérour J (1999) Tetrahedron Lett 40:5853

    Article  CAS  Google Scholar 

  192. Denmark SE, Baird JD, Regens CS (2008) J Org Chem 73:1440

    Article  CAS  Google Scholar 

  193. Denmark SE, Baird JD (2004) Org Lett 6:3649

    Article  CAS  Google Scholar 

  194. Kline T (1985) J Heterocycl Chem 22:505

    Article  CAS  Google Scholar 

  195. Knochel P, Seebach D (1981) Tetrahedron Lett 22:3223

    Article  CAS  Google Scholar 

  196. So CM, Yeung CC, Lau CP, Kwong FY (2008) J Org Chem 73:7803

    Article  CAS  Google Scholar 

  197. Bélanger G, Larouche-Gauthier R, Ménard F, Nantel M, Barabé F (2006) J Org Chem 71:704

    Article  CAS  Google Scholar 

  198. Allison BD, Phuong VK, McAtee LC, Rosen M, Morton M, Prendergast C, Barrett T, Lagaud G, Freedman J, Li L, Wu X, Venkatesan H, Pippel M, Woods C, Rizzolio MC, Hack M, Hoey K, Deng X, King C, Shankley NP, Rabinowitz MH (2006) J Med Chem 49:6371

    Article  CAS  Google Scholar 

  199. Bisseret P, Thielges S, Bourg S, Miethke M, Marahiel MA, Eustache J (2007) Tetrahedron Lett 48:6080

    Article  CAS  Google Scholar 

  200. Vazquez E, Davies IW, Payack JF (2002) J Org Chem 67:7551

    Article  CAS  Google Scholar 

  201. Mizuta M, Seio K, Miyata K, Sekine M (2007) J Org Chem 72:5046

    Article  CAS  Google Scholar 

  202. Molander GA, Canturk B, Kennedy LE (2009) J Org Chem 74:973

    Article  CAS  Google Scholar 

  203. Pagano N, Wong EY, Breiding T, Liu H, Wilbuer A, Bregman H, Shen Q, Diamond SL, Meggers E (2009) J Org Chem 74:8997

    Article  CAS  Google Scholar 

  204. Pagano N, Maksimoska J, Bregman H, Williams DS, Webster RD, Xue F, Meggers E (2007) Org Biomol Chem 5:1218

    Article  CAS  Google Scholar 

  205. Kassis P, Bénéteau V, Mérour J-Y, Routier S (2009) Synthesis 2447

    Google Scholar 

  206. Ishikura M, Uchiyama M, Matsuzaki N (2001) Heterocycles 55:1063

    Article  CAS  Google Scholar 

  207. Ishikura M, Matsuzaki Y, Agata I, Katagiri N (1998) Tetrahedron 54:13929

    Article  CAS  Google Scholar 

  208. Ishikura M, Hino A, Katagiri N (2000) Heterocycles 53:11

    Article  CAS  Google Scholar 

  209. Ishikura M, Imaizumi K, Katagiri N (2000) Heterocycles 53:553

    Article  CAS  Google Scholar 

  210. Ishikura M, Takahashi N, Yamada K, Abe T (2008) Heterocycles 75:107

    Article  CAS  Google Scholar 

  211. Fraley ME, Arrington KL, Buser CA, Ciecko PA, Coll KE, Fernandes C, Hartman GD, Hoffman WF, Lynch JJ, McFall RC, Rickert K, Singh R, Smith S, Thomas KA, Wong BK (2004) Bioorg Med Chem Lett 14:351

    Article  CAS  Google Scholar 

  212. Payack JF, Vazquez E, Matty L, Kress MH, McNamara J (2005) J Org Chem 70:175

    Article  CAS  Google Scholar 

  213. Lötter ANC, Pathak R, Sello TS, Fernandes MA, van Otterlo WAL, de Koning CB (2007) Tetrahedron 63:2263

    Article  CAS  Google Scholar 

  214. de Koning CB, Michael JP, Pathak R, van Otterlo WAL (2004) Tetrahedron Lett 45:1117

    Article  CAS  Google Scholar 

  215. de Koning CB, Michael JP, Rousseau AL (2000) J Chem Soc, Perkin Trans 2 1705

    Google Scholar 

  216. Selvi S, Pu S-C, Cheng Y-M, Fang J-M, Chou P-T (2004) J Org Chem 69:6674

    Article  CAS  Google Scholar 

  217. Kumar A, Say M, Boykin DW (2008) Synthesis 707

    Google Scholar 

  218. Sakamoto T, Kondo Y, Takazawa N, Yamanaka H (1993) Heterocycles 36:941

    Article  CAS  Google Scholar 

  219. Seggio A, Priem G, Chevallier F, Mongin F (2009) Synthesis 3617

    Google Scholar 

  220. L'Helgoual'ch JM, Seggio A, Chevallier F, Yonehara M, Jeanneau E, Uchiyama M, Mongin F (2008) J Org Chem 73:177

    Article  CAS  Google Scholar 

  221. Okada M, Sato I, Cho SJ, Suzuki Y, Ojika M, Dubnau D, Sakagami Y (2004) Biosci Biotechnol Biochem 68:2374

    Article  CAS  Google Scholar 

  222. Daïri K, Yao Y, Faley M, Tripathy S, Rioux E, Billot X, Rabouin D, Gonzales G, Lavallée J-F, Attardo G (2007) Org Proc Res Dev 11:1051

    Article  CAS  Google Scholar 

  223. Johnson CN, Stemp G, Anand N, Stephen SC, Gallagher T (1998) Synlett 1025

    Google Scholar 

  224. James CA, Coelho AL, Gevaert M, Forgione P, Snieckus V (2009) J Org Chem 74:4094

    Article  CAS  Google Scholar 

  225. Beak P, Lee WK (1993) J Org Chem 58:1109

    Article  CAS  Google Scholar 

  226. Peyron C, Benhida R, Bories C, Loiseau PM (2005) Bioorg Chem 33:439

    Article  CAS  Google Scholar 

  227. Pena MA, Sestelo JP, Sarandeses LA (2007) J Org Chem 72:1271

    Article  CAS  Google Scholar 

  228. Bouissane L, Sestelo JP, Sarandeses LA (2009) Org Lett 11:1285

    Article  CAS  Google Scholar 

  229. Jain HD, Zhang C, Zhou S, Zhou H, Ma J, Liu X, Liao X, Deveau AM, Dieckhaus CM, Johnson MA, Smith KS, Macdonald TL, Kakeya H, Osada H, Cook JM (2008) Bioorg Med Chem 16:4626

    Article  CAS  Google Scholar 

  230. Smith AL, Stevenson GI, Lewis S, Patel S, Castro JL (2000) Bioorg Med Chem Lett 10:2693

    Article  CAS  Google Scholar 

  231. Chao W-R, Yean D, Amin K, Green C, Jong L (2007) J Med Chem 50:3412

    Article  CAS  Google Scholar 

  232. Bennasar M-L, Roca T, García-Díaz D (2007) J Org Chem 72:4562

    Article  CAS  Google Scholar 

  233. Bennasar M-L, Roca T, García-Díaz D (2008) J Org Chem 73:9033

    Article  CAS  Google Scholar 

  234. Bennasar M-L, Roca T, García-Díaz D (2008) Synlett 1487

    Google Scholar 

  235. Rawal VH, Cava MP (1986) J Am Chem Soc 108:2110

    Article  CAS  Google Scholar 

  236. Cheng AC, Shulgin AT, Castagnoli N (1982) J Org Chem 47:5258

    Article  CAS  Google Scholar 

  237. Zhao S, Gan T, Yu P, Cook JM (1998) Tetrahedron Lett 39:7009

    Article  CAS  Google Scholar 

  238. Gharpure M, Stoller A, Bellamy F, Firnau G, Snieckus V (1991) Synthesis 1079

    Google Scholar 

  239. Katritzky AR, Faid-Allah H, Marson CM (1987) Heterocycles 26:1333

    Article  CAS  Google Scholar 

  240. Tholander J, Bergman J (1999) Tetrahedron 55:6243

    Article  CAS  Google Scholar 

  241. Bergman J, Wahlström N, Yudina L, Tholander J, Lidgren G (2002) Tetrahedron 58:1443

    Article  CAS  Google Scholar 

  242. Katritzky AR, Le KNB, Mohapatra PP (2007) Synthesis 3141

    Google Scholar 

  243. Katritzky AR, Akutagawa K, Jones RA (1988) Synth Commun 18:1151

    Article  CAS  Google Scholar 

  244. Hudkins RL, Diebold JL, Marsh FD (1995) J Org Chem 60:6218

    Article  CAS  Google Scholar 

  245. Bergman J, Venemalm L (1987) Tetrahedron Lett 28:3741

    Article  CAS  Google Scholar 

  246. Liu Y, Gribble GW (2002) Tetrahedron Lett 43:7135

    Article  CAS  Google Scholar 

  247. Bergman J, Venemalm L (1992) J Org Chem 57:2495

    Article  CAS  Google Scholar 

  248. Liu Y, Gribble GW (2001) Tetrahedron Lett 42:2949

    Article  CAS  Google Scholar 

  249. Shirani H, Stensland B, Bergman J, Janosik T (2006) Synlett 2459

    Google Scholar 

  250. Wincent E, Shirani H, Bergman J, Rannug U, Janosik T (2009) Bioorg Med Chem 17:1648

    Article  CAS  Google Scholar 

  251. Tao M, Park C, Josef K, Hudkins R (2009) J Heterocycl Chem 46:1185

    Article  CAS  Google Scholar 

  252. Hudkins RL, Diebold JL, Angeles TS, Knight E (1997) J Med Chem 40:2994

    Article  CAS  Google Scholar 

  253. Bergman J, Venemalm L (1992) Tetrahedron 48:759

    Article  CAS  Google Scholar 

  254. Bergman J, Venemalm L (1988) Tetrahedron Lett 29:2993

    Article  CAS  Google Scholar 

  255. Ahaidar A, Fernandez D, Perez O, Danelon G, Cuevas C, Manzanares I, Albericio F, Joule JA, Alvarez M (2003) Tetrahedron Lett 44:6191

    Article  CAS  Google Scholar 

  256. Álvarez M, Fernández D, Joule JA (2001) Tetrahedron Lett 42:315

    Article  Google Scholar 

  257. Ahaidar A, Fernández D, Danelón G, Cuevas C, Manzanares I, Albericio F, Joule JA, Álvarez M (2003) J Org Chem 68:10020

    Article  CAS  Google Scholar 

  258. Sakurada J, Satoh T (2007) Tetrahedron 63:3806

    Article  CAS  Google Scholar 

  259. Passarella D, Favia R, Giardini A, Lesma G, Martinelli M, Silvani A, Danieli B, Efange SMN, Mash DC (2003) Bioorg Med Chem 11:1007

    Article  CAS  Google Scholar 

  260. Palmisano G, Santagostino M (1993) Synlett 771

    Google Scholar 

  261. Edwards MP, Doherty AM, Ley SV, Organ HM (1986) Tetrahedron 42:3723

    Article  CAS  Google Scholar 

  262. Ishikura M, Kato H, Ohnuki N (2002) Chem Commun 220

    Google Scholar 

  263. Bernardo PH, Chai CLL, Elix JA (2002) Tetrahedron Lett 43:2939

    Article  CAS  Google Scholar 

  264. Benincori T, Piccolo O, Rizzo S, Sannicoló F (2000) J Org Chem 65:8340

    Article  CAS  Google Scholar 

  265. Kelly TR, Zhao Y, Cavero M, Torneiro M (2000) Org Lett 2:3735

    Article  CAS  Google Scholar 

  266. Kraxner J, Arlt M, Gmeiner P (2000) Synlett 125

    Google Scholar 

  267. Gmeiner P, Kraxner J, Bollinger B (1996) Synthesis 1196

    Google Scholar 

  268. Kraxner J, Gmeiner P (2000) Synthesis 1081

    Google Scholar 

  269. Hlasta DJ, Bell MR (1989) Heterocycles 29:849

    Article  CAS  Google Scholar 

  270. Katritzky AR, Lue P, Chen YX (1990) J Org Chem 55:3688

    Article  CAS  Google Scholar 

  271. Berens U, Brown J, Long J, Selke R (1996) Tetrahedron Asymmetry 7:285

    Article  CAS  Google Scholar 

  272. Kawasaki T, Kodama A, Nishida T, Shimizu K, Somei M (1991) Heterocycles 32:221

    Article  CAS  Google Scholar 

  273. Somei M, Kobayashi T (1992) Heterocycles 34:1295

    Article  CAS  Google Scholar 

  274. Takeda Y, Nishiyama H, Ishikura M, Kamata K, Terashima M (1992) Heterocycles 33:173

    Article  CAS  Google Scholar 

  275. Molina P, Almendros P, Fresneda PM (1993) Tetrahedron Lett 34:4701

    Article  CAS  Google Scholar 

  276. Sanz R, Ignacio JM, Castroviejo MP, Fananas FJ (2007) Arkivoc 84

    Google Scholar 

  277. Rataboul F, Zapf A, Jackstell R, Harkal S, Riermeier T, Monsees A, Dingerdissen U, Beller M (2004) Chem Eur J 10:2983

    Article  CAS  Google Scholar 

  278. Artemova NV, Chevykalova MN, Luzikov YN, Nifant' ev IE, Nifant' ev EE (2004) Tetrahedron 60:10365

    Article  CAS  Google Scholar 

  279. Ruhland T, Pedersen H, Andersen K (2003) Synthesis 2236

    Google Scholar 

  280. Mulvey RE (2009) Acc Chem Res 42:743

    Article  CAS  Google Scholar 

  281. Kondo Y, Yoshida A, Sakamoto T (1996) J Chem Soc, Perkin Trans 1 2331

    Google Scholar 

  282. Dinsmore A, Billing DG, Mandy K, Michael JP, Mogano D, Patil S (2004) Org Lett 6:293

    Article  CAS  Google Scholar 

  283. Naka H, Uchiyama M, Matsumoto Y, Wheatley AEH, McPartlin M, Morey JV, Kondo Y (2007) J Am Chem Soc 129:1921

    Article  CAS  Google Scholar 

  284. Uchiyama M, Naka H, Matsumoto Y, Ohwada T (2004) J Am Chem Soc 126:10526

    Article  CAS  Google Scholar 

  285. Usui S, Hashimoto Y, Morey JV, Wheatley AEH, Uchiyama M (2007) J Am Chem Soc 129:15102

    Article  CAS  Google Scholar 

  286. Ishiyama T, Takagi J, Hartwig JF, Miyaura N (2002) Angew Chem Int Ed 41:3056

    Article  CAS  Google Scholar 

  287. Ishiyama T, Nobuta Y, Hartwig JF, Miyaura N (2003) Chem Commun 2924

    Google Scholar 

  288. Ishiyama T, Takagi J, Nobuta Y, Miyaura N (2005) Org Synth 82:126

    CAS  Google Scholar 

  289. Takagi J, Sato K, Hartwig JF, Ishiyama T, Miyaura N (2002) Tetrahedron Lett 43:5649

    Article  CAS  Google Scholar 

  290. Tagata T, Nishida M (2004) Adv Synth Catal 346:1655

    Article  CAS  Google Scholar 

  291. Lo WF, Kaiser HM, Spannenberg A, Beller M, Tse MK (2007) Tetrahedron Lett 48:371

    Article  CAS  Google Scholar 

  292. Paul S, Chotana GA, Holmes D, Reichle RC, Maleczka RE, Smith MR III (2006) J Am Chem Soc 128:15552

    Article  CAS  Google Scholar 

  293. Kallepalli VA, Shi F, Paul S, Onyeozili EN, Maleczka RE Jr, Smith MR III (2009) J Org Chem 74:9199

    Article  CAS  Google Scholar 

  294. Zhao Z, Snieckus V (2005) Org Lett 7:2523

    Article  CAS  Google Scholar 

  295. Zhao Z, Jaworski A, Piel I, Snieckus V (2008) Org Lett 10:2617

    Article  CAS  Google Scholar 

  296. Klingebiel U, Lüttke W, Noltemeyer M, Schmidt HG (1993) J Organomet Chem 456:41

    Article  CAS  Google Scholar 

  297. Shen K, Fu Y, Li J, Liu L, Guo Q (2007) Tetrahedron 63:1568

    Article  CAS  Google Scholar 

  298. Iwao M, Kuraishi T (1992) Heterocycles 34:1031

    Article  CAS  Google Scholar 

  299. Iwao M, Kuraishi T (1996) Org Synth 73:85

    CAS  Google Scholar 

  300. Meyers AI, Milot G (1993) J Org Chem 58:6538

    Article  CAS  Google Scholar 

  301. Diep V, Dannenberg JJ, Franck RW (2003) J Org Chem 68:7907

    Article  CAS  Google Scholar 

  302. Smith AB, Kürti L, Davulcu AH, Cho YS, Ohmoto K (2007) J Org Chem 72:4611

    Article  CAS  Google Scholar 

  303. Leonori D, Coldham I (2009) Adv Synth Catal 351:2619

    Article  CAS  Google Scholar 

  304. Meyers AI, Hutchings RH (1993) Tetrahedron Lett 34:6185

    Article  CAS  Google Scholar 

  305. Parnes JS, Carter DS, Kurz LJ, Flippin LA (1994) J Org Chem 59:3497

    Article  CAS  Google Scholar 

  306. Govek S, Overman L (2007) Tetrahedron 63:8499

    Article  CAS  Google Scholar 

  307. Overman LE, Peterson EA (2003) Angew Chem Int Ed 42:2525

    Article  CAS  Google Scholar 

  308. Overman LE, Peterson EA (2003) Tetrahedron 59:6905

    Article  CAS  Google Scholar 

  309. Kodanko JJ, Overman LE (2003) Angew Chem Int Ed 42:2528

    Article  CAS  Google Scholar 

  310. Lebsack AD, Link JT, Overman LE, Stearns BA (2002) J Am Chem Soc 124:9008

    Article  CAS  Google Scholar 

  311. Huang A, Kodanko JJ, Overman LE (2004) J Am Chem Soc 126:14043

    Article  CAS  Google Scholar 

  312. Gross KMB, Jun YM, Beak P (1997) J Org Chem 62:7679

    Article  CAS  Google Scholar 

  313. Ahlbrecht H, Schmitt C (1994) Synthesis 983

    Google Scholar 

  314. Davies RP, Raithby PR, Snaith R (1996) Organometallics 15:4355

    Article  CAS  Google Scholar 

  315. Amat M, Coll MD, Bosch J (1995) Tetrahedron 51:10759

    Article  CAS  Google Scholar 

  316. Bergman J, Janosik T, Yudina L, Desarbre E, Lidgren G, Venemalm L (2000) Tetrahedron 56:1911

    Article  CAS  Google Scholar 

  317. Kumar UKS, Patra PK, Ila H, Junjapp H (1998) Tetrahedron Lett 39:2029

    Article  CAS  Google Scholar 

  318. Inagaki S, Nishizawa Y, Sigiura T, Ishihara H (1990) J Chem Soc, Perkin Trans 1 179

    Google Scholar 

  319. Naruse Y, Ito Y, Inagaki S (1991) J Org Chem 56:2256

    Article  CAS  Google Scholar 

  320. Naruse Y, Kido K, Inagaki S (1995) J Org Chem 60:8334

    Article  CAS  Google Scholar 

  321. Fañanás FJ, Granados A, Sanz R, Ignacio JM, Barluenga J (2001) Chem Eur J 7:2896

    Article  Google Scholar 

  322. Barluenga J, Sanz R, Granados A, Fananas FJ (1998) J Am Chem Soc 120:4865

    Article  CAS  Google Scholar 

  323. Comins DL (1992) Synlett 615

    Google Scholar 

  324. Comins DL, Killpack MO (1987) J Org Chem 52:104

    Article  CAS  Google Scholar 

  325. Kitagaki S, Katoh K, Ohdachi K, Takahashi Y, Shibata D, Mukai C (2006) J Org Chem 71:6908

    Article  CAS  Google Scholar 

  326. Buttery CD, Jones RG, Knight DW (1993) J Chem Soc, Perkin Trans 1:1425

    Google Scholar 

  327. Buttery CD, Jones RG, Knight DW (1991) Synlett 315

    Google Scholar 

  328. Fisher LE, Labadie SS, Reuter DC, Clark RD (1995) J Org Chem 60:6224

    Article  CAS  Google Scholar 

  329. Cai X, Snieckus V (2004) Org Lett 6:2293

    Article  CAS  Google Scholar 

  330. Nakagawa K, Somei M (1994) Heterocycles 39:31

    Article  CAS  Google Scholar 

  331. Robaut C, Rivalle C, Rautureau M, Lhoste JM, Bisagni E, Chermann J-C (1985) Tetrahedron 41:1945

    Article  CAS  Google Scholar 

  332. Johnson DA, Gribble GW (1986) Heterocycles 24:2127

    Article  CAS  Google Scholar 

  333. Gribble GW, Johnson DA (1987) Tetrahedron Lett 28:5259

    Article  CAS  Google Scholar 

  334. Lipinska T (2002) Tetrahedron Lett 43:9565

    Article  CAS  Google Scholar 

  335. Grimaldi T, Romero M, Pujol MD (2000) Synlett 1788

    Google Scholar 

  336. Romero M, Pujol MD (2003) Synlett 173

    Google Scholar 

  337. Yokoyama Y, Uchida M, Murakami Y (1989) Heterocycles 29:1661

    Article  CAS  Google Scholar 

  338. Nettekoven M, Psiorz M, Waldmann H (1995) Tetrahedron Lett 36:1425

    Article  CAS  Google Scholar 

  339. Chauder B, Larkin A, Snieckus V (2002) Org Lett 4:815

    Article  CAS  Google Scholar 

  340. Pérez-Serrano L, Casarrubios L, Domínguez G, Freire G, Pérez-Castells J (2002) Tetrahedron 58:5407

    Article  Google Scholar 

  341. Fukuda T, Akashima H, Iwao M (2005) Tetrahedron 61:6886

    Article  CAS  Google Scholar 

  342. Iwao M, Motoi O (1995) Tetrahedron Lett 36:5929

    CAS  Google Scholar 

  343. Iwao M, Motoi O, Fukuda T, Ishibashi F (1998) Tetrahedron 54:8999

    Article  CAS  Google Scholar 

  344. Moro-oka Y, Fukuda T, Iwao M (1999) Tetrahedron Lett 40:1713

    Article  CAS  Google Scholar 

  345. Hayakawa Y, Singh M, Shibata N, Takeuchi Y, Kirk KL (1999) J Fluorine Chem 97:161

    Article  CAS  Google Scholar 

  346. Moro-oka Y, Iwakiri S, Fukuda T, Iwao M (2000) Tetrahedron Lett 41:5225

    Article  CAS  Google Scholar 

  347. Griffen EJ, Roe DG, Snieckus V (1995) J Org Chem 60:1484

    Article  CAS  Google Scholar 

  348. Kinsman A, Snieckus V (1999) Tetrahedron Lett 40:2453

    Article  CAS  Google Scholar 

  349. Rousseau JF, Dodd RH (2001) Heterocycles 55:2289

    Article  CAS  Google Scholar 

  350. Tois J, Koskinen A (2003) Tetrahedron Lett 44:2093

    Article  CAS  Google Scholar 

  351. Schlosser M (2006) Angew Chem Int Ed 45:5432

    Article  CAS  Google Scholar 

  352. Schlosser M, Ginanneschi A, Leroux F (2006) Eur J Org Chem 2956

    Google Scholar 

  353. Parham WE, Bradsher CK (1982) Acc Chem Res 15:300

    Article  CAS  Google Scholar 

  354. Sotomayor N, Lete E (2003) Curr Org Chem 7:275

    Article  CAS  Google Scholar 

  355. Katritzky AR, Xie LH (1995) J Org Chem 60:3707

    Article  CAS  Google Scholar 

  356. Gan T, Liu R, Yu P, Zhao S, Cook JM (1997) J Org Chem 62:9298

    Article  CAS  Google Scholar 

  357. Harper S, Avolio S, Pacini B, Di Filippo M, Altamura S, Tomei L, Paonessa G, Di Marco S, Carfi A, Giuliano C, Padron J, Bonelli F, Migliaccio G, De Francesco R, Laufer F, Rowley M, Narjes F (2005) J Med Chem 48:4547

    Article  CAS  Google Scholar 

  358. Fürstner A, Domostoj MM, Scheiper B (2006) J Am Chem Soc 128:8087

    Article  CAS  Google Scholar 

  359. Herbert JM, Maggiani M (2001) Synth Commun 31:947

    Article  CAS  Google Scholar 

  360. Ueda I, Nishiura M, Takahashi T, Eda K, Hashimoto M, Yamamura K (2006) Tetrahedron Lett 47:8535

    Article  CAS  Google Scholar 

  361. Gribble GW, Saulnier MG (1983) J Org Chem 48:607

    Article  CAS  Google Scholar 

  362. Conway S, Gribble G (1990) Heterocycles 30:627

    Article  CAS  Google Scholar 

  363. Sakamoto T, Kondo Y, Takazawa N, Yamanaka H (1993) Tetrahedron Lett 34:5955

    Article  CAS  Google Scholar 

  364. Amat M, Hadida S, Sathyanarayana S, Bosch J (1994) J Org Chem 59:10

    Article  CAS  Google Scholar 

  365. Koike T, Shinohara Y, Tobinaga S, Tekeuchi N (2000) Heterocycles 53:2701

    Article  CAS  Google Scholar 

  366. Wynne JH, Stalick WM (2002) J Org Chem 67:5850

    Article  CAS  Google Scholar 

  367. Wynne JH, Stalick WM (2003) J Org Chem 68:4845

    Article  CAS  Google Scholar 

  368. Bernardo PH, Chai CLL (2003) J Org Chem 68:8906

    Article  CAS  Google Scholar 

  369. Giordano L, Vermeij RJ, Jares-Erijman EA (2005) Arkivoc 268

    Google Scholar 

  370. Amat M, Seffar F, Llor N, Bosch J (2001) Synthesis 267

    Google Scholar 

  371. Kawasaki I, Katsuma H, Nakayama Y, Yamashita M, Ohta S (1998) Heterocycles 48:1887

    Article  CAS  Google Scholar 

  372. Amat M, Sathyanarayana S, Hadida S, Bosch J (1996) Heterocycles 43:1713

    Article  CAS  Google Scholar 

  373. Amat M, Hadida S, Sathyanarayana S, Bosch J (1997) Org Synth 74:248

    CAS  Google Scholar 

  374. Amat M, Hadida S, Bosch J (1994) Tetrahedron Lett 35:793

    Article  CAS  Google Scholar 

  375. Li G, Wang E, Chen H, Li H, Liu Y, Wang P (2008) Tetrahedron 64:9033

    Article  CAS  Google Scholar 

  376. Sugiyama H, Yokokawa F, Aoyama T, Shioiri T (2001) Tetrahedron Lett 42:7277

    Article  CAS  Google Scholar 

  377. Belsky I, Gertner D, Zilkha A (1968) J Org Chem 33:1348

    Article  CAS  Google Scholar 

  378. Yang YH, Martin AR, Nelson DL, Regan J (1992) Heterocycles 34:1169

    Article  CAS  Google Scholar 

  379. Sauer G, Heidl J, Wachtel H (1988) Tetrahedron Lett 29:6425

    Article  CAS  Google Scholar 

  380. Balle T, Anderson K, Vedsø P (2002) Synthesis 1509

    Google Scholar 

  381. Li L, Martins A (2003) Tetrahedron Lett 44:689

    Article  CAS  Google Scholar 

  382. Li L, Martins A (2003) Tetrahedron Lett 44:5987

    Article  CAS  Google Scholar 

  383. Lachance N, Bonhomme-Beaulieu L, Joly P (2009) Synthesis 721

    Google Scholar 

  384. Buszek K, Luo D, Kondrashov M, Brown N, VanderVelde D (2007) Org Lett 9:4135

    Article  CAS  Google Scholar 

  385. Brown N, Luo D, Decapo J, Buszek K (2009) Tetrahedron Lett 50:7113

    Article  CAS  Google Scholar 

  386. Buszek KR, Brown N, Luo D (2009) Org Lett 11:201

    Article  CAS  Google Scholar 

  387. Brown N, Luo D, Vander Velde D, Yang S, Brassfield A, Buszek K (2009) Tetrahedron Lett 50:63

    Article  CAS  Google Scholar 

  388. Kondo Y, Yoshida A, Sato S, Sakamoto T (1996) Heterocycles 42:105

    Article  CAS  Google Scholar 

  389. Kuethe JT, Comins DL (2004) J Org Chem 69:2863

    Article  CAS  Google Scholar 

  390. Mal S, Bohé L, Achab S (2008) Tetrahedron 64:5904

    Article  CAS  Google Scholar 

  391. Korn TJ, Knochel P (2005) Synlett 1185

    Google Scholar 

  392. Manolikakes G, Knochel P (2009) Angew Chem Int Ed 48:205

    Article  CAS  Google Scholar 

  393. Baron O, Knochel P (2005) Angew Chem Int Ed 44:3133

    Article  CAS  Google Scholar 

  394. Gong LZ, Knochel P (2005) Synlett 267

    Google Scholar 

  395. Kondo Y, Takazawa N, Yoshida A, Sakamoto T (1995) J Chem Soc, Perkin Trans 1:1207

    Google Scholar 

  396. Kasahara T, Kondo Y (2006) Chem Commun 891

    Google Scholar 

  397. Denhart DJ, Deskus JA, Ditta JL, Gao Q, King HD, Kozlowski ES, Meng Z, LaPaglia MA, Mattson GK, Molski TF, Taber MT, Lodge NJ, Mattson RJ, Macor JE (2009) Bioorg Med Chem Lett 19:4031

    Article  CAS  Google Scholar 

  398. Yang X, Althammer A, Knochel P (2004) Org Lett 6:1665

    Article  CAS  Google Scholar 

  399. Yang X, Knochel P (2006) Synthesis 2618

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Hobart and William Smith Colleges, 300 Pulteney St, Geneva, NY, 14456, USA

    Erin T. Pelkey

Authors
  1. Erin T. Pelkey
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Erin T. Pelkey .

Editor information

Editors and Affiliations

  1. Dept. Chemistry, Dartmouth College, Burke Laboratory 6128, Hanover, 03755, New Hampshire, USA

    Gordon W. Gribble

Rights and permissions

Reprints and permissions

Copyright information

© 2010 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Pelkey, E.T. (2010). Metalation of Indole. In: Gribble, G. (eds) Heterocyclic Scaffolds II:. Topics in Heterocyclic Chemistry, vol 26. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2010_56

Download citation

Publish with us

Policies and ethics

Search

Navigation