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Carbene Complexes of Heme Proteins and Iron Porphyrin Models

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Bioorganometallic Chemistry

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 17))

Abstract

The possible formation of carbene complexes of cytochromes P450 enzymes in various metabolisms of xenobiotics is first described. In view of these observations, the organometallic chemistry of iron porphyrins, serving as a basis for elucidating the mechanism of these enzymes is then presented, emphasizing the biological relevance. The chemistry of metalloporphyrin models has been extended to ruthenium and osmium complexes, both metals belonging to the iron triads. This review also illustrates that metalloporphyrins are versatile organometallic catalysts that can be used in many different reactions involving carbene transfer. Their development will be considerably widened in the future, with possible application in asymmetric catalysis.

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Abbreviations

(TPP)H2 :

tetraphenylporphyrin

(TTP)H2 :

tetratolylporphyrin

(TPFPP)H2 :

tetrapentafluorophenylporphyrin

(T-p-ClPP)H2 :

tetra-p-chlorophenylporphyrin

(TMP)H2 :

tetramesitylporphyrin

(OEP)H2 :

octaethylporphyrin

(T-2,6-ClPP)H2 :

tetra-2,6-dichlorophenylporphyrin

(T-p-FPP)H2 :

tetra-p-fluorophenylporphyrin

References

  1. Rickes EL, Brink NG, Koniuszy FR, Wood TR, Folkers K (1948) Science 107:396

    CAS  Google Scholar 

  2. Smith EL, Parker LFJ (1948) Biochem J 43:VIII

    Google Scholar 

  3. Mansuy D, Nastainczyk W, Ullrich V (1974) Naunyn-Schmiedeberg's Arch Pharmakol 285:315

    CAS  Google Scholar 

  4. Mansuy D (1980) Pure Appl Chem 52:681

    CAS  Google Scholar 

  5. Ortiz de Montellano PR, Reich NO (1986) In: Cytochrome P-450, Structure, Mechanism and Biochemistry. Plenum Press, New York, p 281

    Google Scholar 

  6. Wolf CR, Mansuy D, Nastainczyk W, Deutschmann G, Ullrich V (1977) Mol Pharmacol 13:698

    CAS  Google Scholar 

  7. Mansuy D, Battioni JP, Chottard JC, Ullrich V (1979) J Am Chem Soc 101:3971

    CAS  Google Scholar 

  8. Groves JT, Avaria-Neisser GE, Fish KM, Imachi M, Kruczkowski RL (1986) J Am Chem Soc 108:3837

    CAS  Google Scholar 

  9. Mansuy D (1998) Comp Biochem Physiol 121C:5

    Google Scholar 

  10. Mansuy D, Battioni P (2000) In: Kadish KM, Smith KM, Guilard R (eds) The Porphyrin Handbook. Academic Press, San Diego, vol 4, p 1

    Google Scholar 

  11. Meunier B, de Visser SP, Shaik S (2004) Chem Rev 104:3947

    CAS  Google Scholar 

  12. Kadish KM, Smith KM, Guilard RE (2000) The Porphyrin Handbook. Academic Press, Boston, (vols 1–10), vol 1

    Google Scholar 

  13. Guengerich FP (2001) Chem Res Toxicol 14:611

    CAS  Google Scholar 

  14. Ortiz de Montellano PRE (1986) Cytochrome P-450: Structure, Mechanism and Biochemistry. Plenum Press, New York

    Google Scholar 

  15. Ortiz de Montellano PRE (1995) Cytochrome P-450: Structure, Mechanism and Biochemistry. Plenum Press, New York

    Google Scholar 

  16. Mansuy D, Chottard JC, Lange M, Battioni JP (1980) J Mol Catal 7:215

    CAS  Google Scholar 

  17. Mansuy D (1983) Inorg Chim Acta 79:9

    Google Scholar 

  18. Setsune JI, Dolphin D (1987) Can J Chem 65:459

    CAS  Google Scholar 

  19. Pecknagel RO, Glence EAJ (1973) CRC Crit Rev Toxicol 2:263

    Google Scholar 

  20. Ullrich V, Schnabel KH (1973) Drug Metab Disposition 1:176

    CAS  Google Scholar 

  21. Wolf CR, Harrelson WG, Nastainczyk WM, Philpot RM, Kalyanaraman B, Mason RP (1980) Mol Pharmacol 18:553

    CAS  Google Scholar 

  22. Nastainczyk W, Ahr H, Ulrich W (1981) Adv Exper Med Biol 136:799

    Google Scholar 

  23. Wolf CR, Mansuy D, Nastainczyk W, Ullrich V (1978) Biochem Pharmacol 27:240

    Google Scholar 

  24. Hine J, Dowell AM (1954) J Am Chem Soc 76:2688

    CAS  Google Scholar 

  25. Castro CE, Kray JWC (1966) J Am Chem Soc 88:4447

    CAS  Google Scholar 

  26. Mansuy D, Battioni JP (1982) J Chem Soc, Chem Commun:638

    Google Scholar 

  27. Ahr HJ, King LJ, Nastainczyk W, Ullrich V (1982) Biochem Pharmacol 31:383

    CAS  Google Scholar 

  28. Ruf HH, Ahr H, Nastainczyk W, Ullrich V, Mansuy D, Battioni JP, Montiel-Montoya R, Trautwein A (1984) Biochemistry 23:5300

    CAS  Google Scholar 

  29. Castro CE, Bartnicki EW, Belser NO (1978) Biochemistry 17:5582

    Google Scholar 

  30. Castro CE, Wade RS (1985) J Org Chem 50:5342

    CAS  Google Scholar 

  31. Li S, Wackett LP (1993) Biochemistry 32:9355

    CAS  Google Scholar 

  32. Mansuy D, Lange M, Chottard JC, Guerin P, Morliere P, Brault D, Rougee M (1977) J Chem Soc Chem Commun:648

    Google Scholar 

  33. Mansuy D, Lange M, Chottard JC, Bartoli JF, Chevrier B, Weiss R (1978) Angew Chem Int Ed Engl 17:781

    Google Scholar 

  34. Ferrara R, Tolando R, King LJ, Manno M (1997) Toxicol Appl Pharmacol 143:420

    CAS  Google Scholar 

  35. Tolando R, Ferrara R, Eldirdiri NI, King LJ, Manno M (1996) Xenobiotica 26:425

    CAS  Google Scholar 

  36. Luke BT, Loew GH, McLean AD (1987) J Am Chem Soc 109:1307

    CAS  Google Scholar 

  37. Luke BT, Loew GH, McLean AD (1988) J Am Chem Soc 110:3396

    CAS  Google Scholar 

  38. Castro CE, Wade RS, Belser NO (1985) Biochemistry 24:204

    CAS  Google Scholar 

  39. Krone VE, Thauer RK, Hogenkamp HPC, Steinbach K (1991) Biochemistry 30:2713

    CAS  Google Scholar 

  40. Dolbier WRJ, Burkholder CR (1990) J Org Chem 55:589

    CAS  Google Scholar 

  41. Philpot RM, Hogson E (1971) Chem Biol Interact 4:185

    Google Scholar 

  42. Franklin MR (1971) Xenobiotica 1:581

    Article  CAS  Google Scholar 

  43. Mansuy D (1981) Rev Biochem Toxicology 3:283

    CAS  Google Scholar 

  44. Murray M, Wilkinson CF, Marcus C, Dube CE (1983) Mol Pharmacol 24:129

    CAS  Google Scholar 

  45. Chiba M, Nishime JA, Wu-Chen I, Vastag KJ, Sahly YS, Kim BM, Dorsey BD, Vacca JP, Lin JH (1998) Biochem Pharmacol 56:223

    CAS  Google Scholar 

  46. Yu LS, Wilkinson CF, Anders MW (1980) Biochem Pharmacol 29:1113

    CAS  Google Scholar 

  47. Murray M, Hetnarski K, Wilkinson CF (1985) Xenobiotica 15:369

    Article  CAS  Google Scholar 

  48. Baek MS, Kim JY, Myung SW, Yim YH, Jeong JH, Kim DH (2001) Drug Metab Dispos 29:381

    CAS  Google Scholar 

  49. Kumagai Y, Lin LY, Philpot RM, Yamada Y, Oguri K, Yoshimura H, Cho AK (1992) Mol Pharmacol 42:695

    CAS  Google Scholar 

  50. Stewart FHC (1964) Chem Rev 64:129

    CAS  Google Scholar 

  51. White EH, Egger N (1984) J Am Chem Soc 106:3701

    CAS  Google Scholar 

  52. Grab LA, Swanson BA, Ortiz de Montellano PR (1988) Biochemistry 27:4805

    CAS  Google Scholar 

  53. Artaud I, Gregoire N, Leduc P, Mansuy D (1990) J Am Chem Soc 112:6899

    CAS  Google Scholar 

  54. Bartnicki EW, Besler NO, Castro CE (1978) Biochemistry 25:5582

    Google Scholar 

  55. Wade RS, Castro CE (1973) J Am Chem Soc 95:231

    CAS  Google Scholar 

  56. Osawa Y, Highet RJ, Murphy CM, Cotter RJ, Pohl LR (1989) J Am Chem Soc 111:4462

    CAS  Google Scholar 

  57. Tolando R, Cazzaro S, Ferrara R, Rezzadore M, Manno M (1995) Biochem Pharmacol 49:233

    CAS  Google Scholar 

  58. Chiba M, Jin L, Neway W, Vacca JP, Tata JR, Chapman K, Lin JH (2001) Drug Metab Dispos 29:1

    CAS  Google Scholar 

  59. Groves JT, Shalyev K, Lee J (2000) In: Kadish KM, Smith KM, Guilard R (eds) Oxometalloporphyrins in Oxidative Catalysis. The Pophyrin Handbook. Academic Press, San Diego 4:17

    Google Scholar 

  60. Hamaker CG, Mirafzal GA, Woo LK (2001) Organometallics 20:5171

    CAS  Google Scholar 

  61. Li Y, Huang JS, Zhou ZY, Che CM, You XZ (2002) J Am Chem Soc 124:13185

    CAS  Google Scholar 

  62. Fischer EO (1974) Angew Chem Int Ed Engl 86:651

    CAS  Google Scholar 

  63. Schrock RR (1976) J Am Chem Soc 98:5399

    CAS  Google Scholar 

  64. Schrock RR (1979) Acc Chem Res 12:98

    CAS  Google Scholar 

  65. Cardin DJ, Cetinkaya B, Lappert MF (1972) Chem Rev 72:545

    CAS  Google Scholar 

  66. Herrmann WA (1978) Angew Chem Int Ed Engl 17:800

    Google Scholar 

  67. Dotz KH, Fischer H, Hofmann P, Kreissl FR, Schubert U, Weiss K (1983) Transition Metal Carbene Complexes. Verlag Chemie, Weinheim

    Google Scholar 

  68. Brookhart M, Studabaker WB (1987) Chem Rev 87:411

    CAS  Google Scholar 

  69. Demonceau A, Hubert AJ, Noels AF (1991) In: Noels AF, Graziani M, Hubert AJ (eds) Metal Promoted Selectivity in Organic Synthesis. Kluwer Academic Publishers, Dordrecht, p 237

    Google Scholar 

  70. Doyle MP (1994) Comprehensive Organometallic Chemistry II 12:421

    Google Scholar 

  71. Trnka TM, Grubbs RH (2001) Acc Chem Res 34:18

    CAS  Google Scholar 

  72. Tatsumi K, Hoffmann R (1981) Inorg Chem 20:3771

    CAS  Google Scholar 

  73. Brothers PJ, Collman JP (1986) Acc Chem Res 19:209

    CAS  Google Scholar 

  74. English DR, Hendrickson DN, Suslick KS (1983) Inorg Chem 22:367

    CAS  Google Scholar 

  75. Lu D, Paeng IR, Nakamoto K (1991) J Coord Rev 83:3

    Google Scholar 

  76. Chevrier B, Weiss R, Lange M, Chottard JC, Mansuy D (1981) J Am Chem Soc 103:2899

    CAS  Google Scholar 

  77. Ikeno T, Iwakura I, Yamada T (2002) J Am Chem Soc 124:15152

    CAS  Google Scholar 

  78. Iwakura I, Tanaka H, Ikeno T, Yamada T (2004) Chem Lett 33:140

    CAS  Google Scholar 

  79. Brault D, Rougee M, Momenteau M (1971) J Chim Phys 98:1621

    Google Scholar 

  80. Scheidt WR, Reed CA (1981) Chem Rev 81:543

    CAS  Google Scholar 

  81. Scheidt WR (2000) In: Kadish KM, Smith KM, Guilard R (eds) Systematics of the Stereochemistry of Porphyrins and Metalloporphyrins. The Porphyrin Handbook. Academic Press, San Diego CA 3:49

    Google Scholar 

  82. Chottard G, Battioni P, Battioni JP, Lange M, Mansuy D (1981) Inorg Chem 20:1718

    CAS  Google Scholar 

  83. Mansuy D, Guerin P, Chottard JC (1979) J Organometal Chem 171:195

    CAS  Google Scholar 

  84. Mansuy D, Lange M, Chottard JC (1978) J Am Chem Soc 100:3213

    CAS  Google Scholar 

  85. Battioni JP, Mansuy D, Chottard JC (1980) Inorg Chem 19:791

    CAS  Google Scholar 

  86. Battioni JP, Chottard JC, Mansuy D (1982) Inorg Chem 21:2056

    CAS  Google Scholar 

  87. Mansuy D, Lecomte JP, Chottard JC, Bartoli JF (1981) Inorg Chem 20:3119

    CAS  Google Scholar 

  88. Goedken VL, Deakin MR, Bottomley LA (1982) J Chem Soc:607

    Google Scholar 

  89. Battioni JP, Dupre D, Mansuy D (1981) J Organometal Chem 214:303

    CAS  Google Scholar 

  90. Beck W, Knauer W, Robl C (1990) Angew Chem Int Ed Engl 29:318

    Google Scholar 

  91. Mansuy D, Lange M, Chottard JC (1979) J Am Chem Soc 101:6437

    CAS  Google Scholar 

  92. Latos-Grazynski L, Cheng RJ, La Mar GN, Balch AL (1981) J Am Chem Soc 103:4270

    CAS  Google Scholar 

  93. Balch AL, Cheng RJ, La Mar GN, Latos-Grazynski L (1985) Inorg Chem 24:2651

    CAS  Google Scholar 

  94. Olmstead MM, Cheng RJ, Balch AL (1982) Inorg Chem 21:4143

    CAS  Google Scholar 

  95. Mansuy D, Morgenstern-Badarau I, Lange M, Gans P (1982) Inorg Chem 21:1427

    CAS  Google Scholar 

  96. Ortiz de Montellano PR, Grab LA (1986) J Am Chem Soc 108:5584

    CAS  Google Scholar 

  97. Artaud I, Gregoire N, Battioni JP, Dupré D, Mansuy D (1988) J Am Chem Soc 110:8714

    CAS  Google Scholar 

  98. Chevrier B, Weiss R (1976) J Am Chem Soc 98:2985

    CAS  Google Scholar 

  99. Loew GH, Herman ZS, Rhomer M, Goldblum A, Pudzianowski A (1981) Ann NY Acad Sci 367:192

    CAS  Google Scholar 

  100. Lange M, Battioni JP, Mansuy D, Lexa D, Saveant JM (1981) J Chem Soc, Chem Commun:888

    Google Scholar 

  101. Hanson LK, Eaton WA, Sligar SG, Gunsalus IC, Gouterman M, Connell CR (1976) J Am Chem Soc 98:2672

    CAS  Google Scholar 

  102. Guerin P, Battioni JP, Chottard JC, Mansuy D (1981) J Organometal Chem 218:201

    CAS  Google Scholar 

  103. Mansuy D, Battioni JP, Chottard JC (1978) J Am Chem Soc 100:4311

    CAS  Google Scholar 

  104. Balch AL, Chan YW, La Mar GN, Latos-Grazynski L, Renner MW (1985) Inorg Chem 24:1437

    CAS  Google Scholar 

  105. Wisnieff TJ, Gold A, Evans JSA (1981) J Am Chem Soc 103:5616

    CAS  Google Scholar 

  106. Mansuy D, Lange M, Chottard JC, Bartoli JF (1978) Tetrahedron Lett:3027

    Google Scholar 

  107. Bruice TC, Furter PG, Ball SS (1981) J Am Chem Soc 103:4578

    CAS  Google Scholar 

  108. Batten P, Hamilton AL, Johnson AW, Mahendran M, Ward D, King TJ (1977) J Chem Soc Perkin 1:1623

    Google Scholar 

  109. Johnson A, Ward D, Batten P, Hamilton AL, Shelton G, Elson CM (1975) J Chem Soc, Perkin Trans 1:2076

    Google Scholar 

  110. Ziegler CJ, Suslick KS (1996) J Am Chem Soc 118:5306

    CAS  Google Scholar 

  111. Ziegler CJ, Suslick KS (1997) J Organometal Chem 528:83

    CAS  Google Scholar 

  112. Crabtree RH (1994) Organometallic Chemistry of The Transition Metals, 2nd edn. Wiley, New York

    Google Scholar 

  113. Rooney AD, McGarvey JJ, Gordon KC (1995) Organometallics 14:107

    CAS  Google Scholar 

  114. Pourreau DB, Geoffroy GL (1985) Adv Organometal Chem 24:249

    Article  CAS  Google Scholar 

  115. Battioni JP, Lexa D, Mansuy D, Saveant JM (1983) J Am Chem Soc 105:207

    CAS  Google Scholar 

  116. Lexa D, Saveant JM, Battioni JP, Lange M, Mansuy D (1981) Angew Chem Int Ed Engl 20:578

    Google Scholar 

  117. Guilard R, Tabard A, Van Caemelbecke E, Kadish KM (2000) The Porphyrin Handbook 3:295

    CAS  Google Scholar 

  118. Setsune JI, Iida T, Kitao T (1988) Tetrahedron Lett 29:5677

    CAS  Google Scholar 

  119. Buschman J, Angst W, Schwarzenbach RP (1999) Environ Sci Technol 33:1015

    Google Scholar 

  120. Chan YW, Renner MW, Balch AL (1983) Organometallics 2:1888

    CAS  Google Scholar 

  121. Lange M, Mansuy D (1981) Tetrahedron Lett 22:2561

    CAS  Google Scholar 

  122. Chan YW, Wood FE, Renner MW, Hope H, Balch A (1984) J Am Chem Soc 106:3380

    CAS  Google Scholar 

  123. Balch AL, Chan YW, Olmstead MM, Renner MW, Wood FE (1988) J Am Chem Soc 110:3897

    CAS  Google Scholar 

  124. Collman JP, Barnes CE, Swepston PN, Ibers JA (1984) J Am Chem Soc 106:3500

    CAS  Google Scholar 

  125. Collman JP, Brothers PJ, McElwee-White L, Rose E (1985) J Am Chem Soc 107:6110

    CAS  Google Scholar 

  126. Collman JP, Brothers PJ, McElwee-White L, Rose E, Wright LJ (1985) J Am Chem Soc 107:4570

    CAS  Google Scholar 

  127. Collman JP, McElwee-White L, Brothers PJ, Rose E (1986) J Am Chem Soc 108:1332

    CAS  Google Scholar 

  128. Collman JP, Rose E, Venburg GD (1993) J Chem Soc, Chem Commun:934

    Google Scholar 

  129. Camenzind MJ, James BR, Dolphin D (1986) J Chem Soc, Chem Commun:1137

    Google Scholar 

  130. Rajapakse N, James BR, Dolphin D (1990) Can J Chem 68:2274

    CAS  Google Scholar 

  131. Setsune JI, Yoshida ZI, Ogoshi H (1982) J Chem Soc, Perkin Trans 1:983

    Google Scholar 

  132. Bonomo L, Stern C, Solari E, Scopelliti R, Floriani C (2001) Angew Chem Int Ed 40:1449

    CAS  Google Scholar 

  133. Galardon E, Le Maux P, Toupet L, Simonneaux G (1998) Organometallics 17:565

    CAS  Google Scholar 

  134. Nishiyama H, Aoki K, Itoh H, Iwamura T, Sakata N, Kurihara O, Motoyama Y (1996) Chem Lett:1071

    Google Scholar 

  135. Galardon E, Le Maux P, Simonneaux G (1997) J Chem Soc, Chem Commun:927

    Google Scholar 

  136. Djukic JP, Smith DA, Young VG, Woo LK (1994) Organometallics 13:3020

    CAS  Google Scholar 

  137. Boschi T, Licoccia S, Paolesse R, Tagliatesta P, Pelizzi G, Vitali F (1989) Organometallics 8:330

    CAS  Google Scholar 

  138. Nguyen ST, Johnson LK, Grubbs RH (1992) J Am Chem Soc 114:3974

    CAS  Google Scholar 

  139. Adams H, Bailey NA, Ridgway C, Taylor BF, Walter SJ, Winter MJ (1990) J Organometal Chem 394:349

    CAS  Google Scholar 

  140. Che CM, Huang JS, Lee FW, Li Y, Lai TS, Kwong HL, Teng PF, Lee WS, Lo WC, Peng SM, Zhou ZY (2001) J Am Chem Soc 123:4119

    CAS  Google Scholar 

  141. Li Y, Huang JS, Xu GB, Zu N, Zhou ZY, Che CM, Wong KY (2004) Chem Eur J 10:3486

    CAS  Google Scholar 

  142. Kawai M, Yuge H, Miyamoto TK (2002) Acta Cryst Sec C 58:m581

    Google Scholar 

  143. Harada T, Wada S, Yuge H, Miyamoto TK (2003) Acta Cryst Sec C 59:m37

    Google Scholar 

  144. Wada S, Yuge H, Miyamoto TK (2003) Acta Cryst Sec C 59:m369

    Google Scholar 

  145. Seyler JW, Safford LK, Fanwick PE, Leidner CR (1992) Inorg Chem 31:1545

    CAS  Google Scholar 

  146. Ke M, Rettig SJ, James BR, Dolphin D (1987) Chem Soc, Chem Commun:1110

    Google Scholar 

  147. Schrock RR (1975) J Am Chem Soc 97:6577

    CAS  Google Scholar 

  148. Tilset M, Bodner GS, Senn DR, Gladysz JA, Parker VD (1987) J Am Chem Soc 109:7551

    CAS  Google Scholar 

  149. Woo LK, Smith DA (1992) Organometallics 11:2344

    CAS  Google Scholar 

  150. Woo LK, Smith DA, Young VG (1991) Organometallics 10:3977

    CAS  Google Scholar 

  151. Djukic JP, Young VG, Woo LK (1994) Organometallics 13:3995

    CAS  Google Scholar 

  152. Li Y, Huang JS, Zhou ZY, Che CM (2001) J Am Chem Soc 123:4843

    CAS  Google Scholar 

  153. Li Y, Huang JS, Zhou ZY, Che CM (2003) J Chem Soc, Chem Commun:1362

    Google Scholar 

  154. Sawano K, Yuge H, Miyamoto TK (2005) Inorg Chim Acta 358:1830

    CAS  Google Scholar 

  155. Nishiyama H, Itoh Y, Matsumoto H, Park SB, Itoh K (1994) J Am Chem Soc 116:2223

    CAS  Google Scholar 

  156. Nishiyama H, Itoh Y, Suwagara Y, Matsumoto H, Aoki K, Itoh K (1995) Bull Chem Soc Jpn 68:1247

    CAS  Google Scholar 

  157. Doyle MP, Forbes DC (1998) Chem Rev 98:911

    CAS  Google Scholar 

  158. Callot HJ, Piechocki C (1980) Tetrahedron Lett 21:3489

    CAS  Google Scholar 

  159. Callot HJ, Metz F, Piechocki C (1982) Tetrahedron 38:2365

    CAS  Google Scholar 

  160. Brown KC, Kodadek T (1992) J Am Chem Soc 114:8336

    CAS  Google Scholar 

  161. Maxwell JL, Brown KC, Bartley DW, Kodadek T (1992) Science 256:1544

    CAS  Google Scholar 

  162. Maxwell JL, O'Malley S, Brown KC, Kodadek T (1992) Organometallics 11:645

    CAS  Google Scholar 

  163. O'Malley S, Kodadek T (1992) Organometallics 11:2299

    Google Scholar 

  164. Bartley DW, Kodadek T (1993) J Am Chem Soc 115:1656

    CAS  Google Scholar 

  165. Yang J, Breslow R (2000) Tetrahedron Lett 41:8063

    CAS  Google Scholar 

  166. Barrett AGM, Braddock DG, Lenoir I, Tone I (2001) J Org Chem 66:8260

    CAS  Google Scholar 

  167. Doyle MP (1986) Chem Rev 86:919

    CAS  Google Scholar 

  168. Smith DA, Reynolds DN, Woo LK (1993) J Am Chem Soc 115:2511

    CAS  Google Scholar 

  169. Hamaker CG, Djukic JP, Smith DA, Woo LK (2001) Organometallics 20:5189

    CAS  Google Scholar 

  170. Wolf JR, Hamaker CG, Djukic JP, Kodadek T, Woo LK (1995) J Am Chem Soc 117:9194

    CAS  Google Scholar 

  171. Lo WC, Che CM, Cheng KF, Mak TCW (1997) J Chem Soc, Chem Commun:1205

    Google Scholar 

  172. Galardon E, Le Maux P, Simonneaux G (1997) J Chem Soc, Perkin Trans 1:2455

    Google Scholar 

  173. Galardon E, Le Maux P, Simonneaux G (2000) Tetrahedron 56:615

    CAS  Google Scholar 

  174. Zheng SL, Yu WY, Che CM (2002) Org Lett 4:889

    CAS  Google Scholar 

  175. Le Maux P, Bahri H, Simonneaux G (1991) J Chem Soc Chem Commun:1350

    Google Scholar 

  176. Halterman RL, Jan ST (1991) J Org Chem 56:5253

    CAS  Google Scholar 

  177. Ini S, Kapon M, Cohen S, Gross Z (1996) Tetrahedron: Asymmetry 7:659

    CAS  Google Scholar 

  178. Lai TS, Kwong HL, Zhang R, Che CM (1998) J Chem Soc, Dalton Trans:3559

    Google Scholar 

  179. Gross Z, Ini S, Kapon M, Cohen S (1996) Tetrahedron Lett 37:7325

    CAS  Google Scholar 

  180. Berkessel A, Frauenkron M (1997) J Chem Soc, Perkin Trans:2265

    Google Scholar 

  181. Frauenkron M, Berkessel A (1997) Tetrahedron Lett 38:7175

    CAS  Google Scholar 

  182. Gross Z, Galili N, Simkhovich L (1999) Tetrahedron Lett 40:1571

    CAS  Google Scholar 

  183. Zhang JL, Chan PWH, Che CM (2003) Tetrahedron Lett 44:8733

    CAS  Google Scholar 

  184. Ferrand Y, Poriel C, Le Maux P, Rault-Berthelot J, Simonneaux G (2005) Tetrahedron Asymmetry 16:1463

    CAS  Google Scholar 

  185. Ferrand Y, Le Maux P, Simonneaux G (2005) Tetrahedron Asymmetry 16:3829

    CAS  Google Scholar 

  186. Zhang JL, Liu YL, Che CM (2002) Chem Commun: 2906

    Google Scholar 

  187. Poriel C, Ferrand Y, Le Maux P, Paul C, Rault-Berthelot J, Simonneaux G (2003) Chem Commun:2308

    Google Scholar 

  188. Paul-Roth C, Rault-Berthelot J, Simonneaux G (2004) Tetrahedron 60:12169

    CAS  Google Scholar 

  189. Callot H, Metz F (1982) Tetrahedron Lett 23:4321

    CAS  Google Scholar 

  190. Hayashi T, Kato T, Kaneko T, Asai T, Ogoshi H (1994) J Organometal Chem 473:323

    CAS  Google Scholar 

  191. Galardon E, Roué S, Le Maux P, Simonneaux G (1998) Tetrahedron Lett 39:2333

    CAS  Google Scholar 

  192. Zheng SL, Yu WL, Xu MX, Che CM (2003) Tetrahedron Lett 44:1445

    CAS  Google Scholar 

  193. Cheung WH, Zheng SL, Yu WY, Zhou GC, Che CM (2003) Org Lett 5:2535

    CAS  Google Scholar 

  194. Simonneaux G, Galardon E, Paul-Roth C, Gulea M, Masson S (2001) J Organometal Chem 617–618:360

    Google Scholar 

  195. Zhou CY, Yu WY, Chan PWH, Che CM (2004) J Org Chem 69:7072

    CAS  Google Scholar 

  196. Mirafzal GA, Cheng G, Woo LK (2002) J Am Chem Soc 124:176

    CAS  Google Scholar 

  197. Fujimura O, Honma T (1998) Tetrahedron Lett 39:625

    CAS  Google Scholar 

  198. Shen Y, Zhang Y, Zhou Y (1998) J Chem Soc, Chem Commun:2195

    Google Scholar 

  199. Aggarwal VK, Fulton JR, Sheldon CG, de Vicente J (2003) J Am Chem Soc 125:6034

    CAS  Google Scholar 

  200. Zhou CY, Yu WY, Che CM (2002) Org Lett 4:3235

    CAS  Google Scholar 

  201. Zhou CY, Chan PWH, Yu WY, Che CM (2003) Synthesis 9:1403

    Google Scholar 

  202. Li GY, Che CM (2004) Org Lett 6:1621

    CAS  Google Scholar 

  203. Tatsumi K, Hoffmann R, Whangbo MH (1980) J Chem Soc, Chem Commun:509

    Google Scholar 

  204. Simonneaux G, Le Maux P (2002) Coord Chem Rev 228:43

    CAS  Google Scholar 

  205. Che CM, Huang JS (2002) Coord Chem Rev 231:151

    CAS  Google Scholar 

  206. Paulson DR, Addison AW, Dolphin D, James BR (1979) J Biol Chem 254:7002

    CAS  Google Scholar 

  207. Srivastava TS (1981) Inorg Chim Acta 55:161

    CAS  Google Scholar 

  208. Ishimori K, Morishima I (1988) Biochemistry 27:4060

    CAS  Google Scholar 

  209. Morishima I, Shiro Y, Nakajima K (1986) Biochemistry 25:3576

    CAS  Google Scholar 

  210. Lu Y, Berry SM, Pfister TD (2001) Chem Rev 101:3047

    CAS  Google Scholar 

  211. Ozaki S, Matsui T, Roach MP, Watanabe Y (2000) Coord Chem Rev 198:39

    CAS  Google Scholar 

  212. Hayashi T, Hisaeda Y (2002) Acc Chem Res 35:35

    CAS  Google Scholar 

  213. Yamamoto Y, Nagao S, Hirai Y, Inose T, Terui N, Mita H, Suzuki A (2004) J Biol Inorg Chem 9:152

    CAS  Google Scholar 

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  1. Laboratoire de Sciences Chimiques de Rennes, UMR CNRS 6226, Université de Rennes 1, 35042, Rennes cedex, France

    Gérard Simonneaux & Paul Le Maux

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  1. Gérard Simonneaux
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  2. Paul Le Maux
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Simonneaux, G., Le Maux, P. Carbene Complexes of Heme Proteins and Iron Porphyrin Models. In: Simonneaux, G. (eds) Bioorganometallic Chemistry. Topics in Organometallic Chemistry, vol 17. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3418_006

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