Skip to main content
SpringerLink
Log in

Organocatalysed Asymmetric Oxidation Reactions

  • Chapter
  • First Online:
Enantioselective Organocatalyzed Reactions I

Abstract

This review highlights the progress of highly enantioselective ­organocatalytic systems for asymmetric oxidation. For example, since the first reported enantioselective dioxirane catalysts developed independently by Curci and Marples, several systems have been developed which give greater than 90% ee for ­epoxidation. Dioxiranes have also been used for a range of other oxidation reactions including C–H oxidation. Oxaziridines have been widely used for the enantioselective oxidation of sulfides, alkenes and they have recently been reported, for the first time, to catalyse the epoxidation and C–H hydroxylation of a range of substrates. Oxaziridinium salts, the quaternised analogues of oxaziridines are prepared in situ from the corresponding iminium ions and ees of up to 97% have been achieved. The epoxidation of α,β-unsaturated ketones has been successfully achieved using asymmetric phase transfer catalysis and in situ amine/enamine catalysis.

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 129.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 169.99
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. Benedetti F, Berti F, Norbedo S (1998) Tetrahedron Lett 39:7971

    Article  CAS  Google Scholar 

  2. O’Brien P, de Sousa SE, Poumellec P (1998) J Chem Soc Perkin Trans 1:1483

    Google Scholar 

  3. (a) Zwanenburg B, Legters J, Thijis L (1989) Tetrahedron Lett 30:4881; (b) Zwanenburg B, Grijzen Y, Thijis L, Gentilucci L (1995) Tetrahedron Lett 36:4665

    Google Scholar 

  4. Bartok M, Lang KL (1985) In: Hassner A (ed.) Small ring heterocycles, vol 42, Part 3, Wiley Interscience, Weinheim

    Google Scholar 

  5. Plesnicar B (1983) In: Patai S (ed) The chemistry of peroxides, Wiley, New York, p 521

    Google Scholar 

  6. (a) Houk KN, Liu J, DeMello NC, Condroski KR (1997) J Am Chem Soc 119:10147; (b) Washington I, Houk KN (2000) J Am Chem Soc 122:2948

    Google Scholar 

  7. Payne GB, Denning PH, Williams PH (1961) J Org Chem 26:659

    Article  CAS  Google Scholar 

  8. Payne GB (1962) Tetrahedron 18:763

    Article  CAS  Google Scholar 

  9. (a) Henbest HB (1965) Chem Soc Spec Publ 19:83; (b) Ewins RC, Henbest HB, Mckervey MA (1967) J Chem Soc Chem Commun 1085; (c) Pirkle WH, Rinaldi PL (1977) J Org Chem 42:2080; (d) Montanari FJ (1969) J Chem Soc Chem Commun 135; (e) Bowman RM, Collins JF, Grundon MF (1973) J Chem Soc Perkin Trans 1:626; (f) Bowman R M, Collins JF, Grundon MF (1967) J Chem Soc Chem Commun 1131; (g) Morrison JD, Mosher HS (1971) Asymmetric Organic Reactions, American Chemical Society, Washington DC, p 336

    Google Scholar 

  10. Hassine B, Gorsane M, Geerts-Evrard F, Pecher J, Martin RH, Castelet D (1986) Bull Soc Chim Belg 95:547

    Article  Google Scholar 

  11. Hassine B, Gorsane M, Pecher J, Martin RH (1986) Bull Soc Chim Belg 95:557

    Article  Google Scholar 

  12. Juliá S, Masana J, Vega JC (1980) Angew Chem Int Ed 19:929

    Article  Google Scholar 

  13. (a) Bentley PA, Bergeron S, Cappi MW, Hibbs DE, Hursthouse MB, Nugent TC, Pulido R, Roberts SM, Wu LE (1997) J Chem Soc Chem Commun 739; (b) Allen JV, Cappi MW, Kary PD, Roberts SM, Williams NM, Wu LE (1997) J Chem Soc Perkin Trans 1:3297; (c) Adger BM, Barkley JV, Bergeron S, Cappi MW, Flowerdew BE, Jackson MP, McCague R, Nugent TC, Roberts SM (1997) J Chem Soc Perkin Trans 1:3501

    Google Scholar 

  14. (a) Gilmore AT, Roberts SM, Hursthouse MB, Abdul-Malik, KM (1998) Tetrahedron Lett 39:3315; (b) Allen JV, Bergeron S, Griffiths MJ, Mukherjee S, Roberts SM, Williamson NM, Wu LE (1998) J Chem. Soc Perkin Trans 1:3171

    Google Scholar 

  15. (a) Mazaleyrat JP (1983) Tetrahedron Lett 24:1243; (b) Baba N, Oda J, Kawaguchi M (1986) Agric Biol Chem 50:3113; (c) Shi M, Masaki Y (1994) J Chem Res (S) 250; (d) Shi M, Kazuta K, Satoh Y, Masaki Y (1994) Chem Pharm Bull 42:2625

    Google Scholar 

  16. (a) Helder R, Hummelen JC, Laane RWPM, Wiering JS, Wynberg H (1976) Tetrahedron Lett 17:1831; (b) Wynberg H, Gerijdanus B (1978) J Chem Soc Chem Commun 427; (c) Marsman B, Wynberg H (1979) J Org Chem 44:2312

    Google Scholar 

  17. Lygo B, Wainwright PG (1998) Tetrahedron Lett 39:1599

    Article  CAS  Google Scholar 

  18. (a) Adam W, Bheema Roa P, Degen H-G, Levai A, Patonay T, Saha-Möller CR (2002) J Org Chem 67:259; (b) Adam W, Bheema Roa P, Degen H-G, Saha-Möller C R (2001) Tetrahedron: Asymm 12:121

    Google Scholar 

  19. Curci R, Fiorentino M, Serio MR (1984) J Chem Soc Chem Commun 155

    Google Scholar 

  20. Curci R, D’Accolti L, Fiorentino M, Rosa A (1995) Tetrahedron Lett 36:2437

    Article  Google Scholar 

  21. Brown DS, Marples BA, Smith P, Walton L (1995) Tetrahedron 51:3587

    Article  CAS  Google Scholar 

  22. Yang D, Yip Y-C, Tang M-W, Wong M-K, Zheng J-H, Cheung K-K (1996) J Am Chem Soc 118:491

    Article  CAS  Google Scholar 

  23. Yang D, Wang XC, Wong M-K, Yip Y-C, Tang M-W (1996) J Am Chem Soc 118:11311

    Google Scholar 

  24. Yang D, Wong M-K, Yip Y-C, Wang XC, Tang M-W, Zheng J-H, Cheung K-K (1998) J Am Chem Soc 120:5943

    Google Scholar 

  25. Denmark SE, Forbs DC, Hays DS, DePue JS, Wilde RG (1995) J Org Chem 60:1391

    Article  CAS  Google Scholar 

  26. Denmark SE, Wu Z (1999) Synlett 847

    Google Scholar 

  27. Denmark SE, Wu Z, Crudden C, M, Matsuhashi H (1997) J Org Chem 62:8288

    Google Scholar 

  28. Denmark SE, Matsuhashi H (2002) J Org Chem 67:3479

    Article  CAS  Google Scholar 

  29. Song CE, Kim YH, Lee KC, Lee S-G, Jin BW (1997) Tetrahedron 53:2921

    Google Scholar 

  30. Adam W, Zaho C-G (1997) Tetrahedron: Asymm 8:3995

    Article  CAS  Google Scholar 

  31. Armstrong A, Hayter BR (1998) Chem Commun 621

    Google Scholar 

  32. Tu Y, Wang Z-X, Shi Y (1996) J Am Chem Soc 118:9806

    Article  CAS  Google Scholar 

  33. Wang Z-X, Tu Y, Frohn M, Shi Y (1997) J Org Chem 62:2328

    Article  CAS  Google Scholar 

  34. Frohn M, Shi Y (1997) J Org Chem 62:2328

    Article  Google Scholar 

  35. Wang Z-X, Shi Y (1997) J Org Chem 62:8622

    Article  CAS  Google Scholar 

  36. Wang Z-X, Shi Y (1998) J Org Chem 63:3099

    Article  CAS  Google Scholar 

  37. Zhu Y, Tu Y, Yu H, Shi Y (1998) Tetrahedron Lett 39:7819

    Article  CAS  Google Scholar 

  38. Warren JD, Shi Y (1999) J Org Chem 64:7675

    Article  CAS  Google Scholar 

  39. Tian H, She X, Shu L, Yu H, Shi Y (2000) J Am Chem Soc 122:2435

    Article  Google Scholar 

  40. Tian H, She X, Yu H, Shu L, Shi Y (2002) J Org Chem 67:2435

    Article  CAS  Google Scholar 

  41. Tian H, She X, Xu J, Shi Y (2001) Org Lett 3:1929

    Article  CAS  Google Scholar 

  42. Cao GA, Wang Z-X, Tu Y, Shi Y (1998) Tetrahedron Lett 39:4425

    Google Scholar 

  43. Frohn M, Zhou X, Zhang J-R, Tang Y, Shi Y (1999) J Am Chem Soc 121:7718

    Article  CAS  Google Scholar 

  44. Shu L, Shi Y (1999) Tetrahedron Lett 40:8721

    Article  CAS  Google Scholar 

  45. Shu L, Shi Y (2000) J Org Chem 65:8807

    Article  CAS  Google Scholar 

  46. Wu X-Y, She X, Shi Y (2002) J Am Chem Soc 124:8792

    Article  CAS  Google Scholar 

  47. Burke CP, Shi Y (2007) J Org Chem 72:4093

    Article  CAS  Google Scholar 

  48. Burke CP, Shu L, Shi Y (2007) J Org Chem 72:6320

    Article  CAS  Google Scholar 

  49. Ager DJ, Anderson K, Oblinger E, Shi Y, VanderRoest J (2007) Org Process Res Dev 11:44

    Article  CAS  Google Scholar 

  50. (a) Xiong Z, Corey EJ (2000) J Am Chem Soc 122:4831; (b) Xiong Z, Corey EJ (2000) J Am Chem Soc 122:9328

    Google Scholar 

  51. Davis FA, Abdul-Malik NF, Awad SB, Haracal ME (1981) Tetrahedron Lett 22:917

    Article  CAS  Google Scholar 

  52. Davis FA, Towson JC, Weismiller MC, Lal S, Caroll PJ (1988) J Am Chem Soc 110:8477

    Article  CAS  Google Scholar 

  53. Page PCB, Heer JP, Bethell D, Lund A, Collington EW, Andrews DM (1997) J Org Chem 62:6093

    Article  CAS  Google Scholar 

  54. Davis FA, Haracal ME, Awad SB (1983) J Am Chem Soc 105:3123

    Article  CAS  Google Scholar 

  55. Davis FA, Przeslawski RM (1991) In: Abstracts of papers of 201st national meeting of the American Chemical Society, Atlanta, American Chemical Society, Washinghton, DC, 1991, ORGN 0105

    Google Scholar 

  56. Davis FA, Haque MS (1986) J Org Chem 51:4083

    Article  CAS  Google Scholar 

  57. Davis FA, Vishwakarma LC, Billmers JM (1984) J Org Chem 49:3241

    Article  CAS  Google Scholar 

  58. Brook AG, MaCrae OM (1974) J Organomet Chem 77:C19

    Article  CAS  Google Scholar 

  59. Adam W, Fell RT, Saha-Möller CR, Zhao C-G (1998) Tetrahedron: Asymm 9:397

    Google Scholar 

  60. Davis FA, Sheppard AC (1987) J Org Chem 52:954

    Article  CAS  Google Scholar 

  61. Brodsky BH, Du Bois J (2005) J Am Chem Soc 127:15391

    Article  CAS  Google Scholar 

  62. Milliet P, Picot A, Lusinchi X (1976) Tetrahedron Lett 17:1573

    Article  Google Scholar 

  63. Milliet P, Picot A, Lusinchi X (1976) Tetrahedron Lett 17:1577

    Article  Google Scholar 

  64. Milliet P, Picot A, Lusinchi X (1981) Tetrahedron 24:4201

    Article  Google Scholar 

  65. Hanquet G, Lusinchi X, Milliet P (1987) Tetrahedron Lett 28:6061

    Article  CAS  Google Scholar 

  66. Hanquet G, Lusinchi X, Milliet P (1988) Tetrahedron Lett 29:3941

    Article  CAS  Google Scholar 

  67. Lusinchi X, Hanquet G (1997) Tetrahedron 53:13727

    Article  CAS  Google Scholar 

  68. Hanquet G, Lusinchi X, Milliet P (1993) Tetrahedron Lett 34:7271

    Article  Google Scholar 

  69. Bohé L, Lusinchi M, Lusinchi X (1999) Tetrahedron 55:155

    Article  Google Scholar 

  70. Hanquet G, Lusinchi X (1994) Tetrahedron 50:12185

    Article  CAS  Google Scholar 

  71. Chiaroni A, Hanquet G, Lusinchi M, Riche C (1993) Acta Crystallogr Sect C 51:2047

    Article  Google Scholar 

  72. Aggarwal VK, Wang MF (1996) J Chem Soc Chem Commun 191

    Google Scholar 

  73. Armstrong A, Ahmed G, Garnett I, Goacolou K (1997) Synlett 1075

    Google Scholar 

  74. Armstrong A, Ahmed G, Garnett I, Goacolou K, Wailes JS (1999) Tetrahedron 55:2341

    Article  CAS  Google Scholar 

  75. Minakata S, Takemiya A, Nakamura K, Ryu I, Komatsu M (2000) Synlett 1810

    Google Scholar 

  76. Wong M-K, Ho L-M, Zheng Y-S, Ho C-Y, Yang D (2001) Org Lett 3:2587

    Article  CAS  Google Scholar 

  77. Armstrong A, Draffan AG (1998) Synlett 646

    Google Scholar 

  78. Armstrong A, Draffan AG (1999) Tetrahedron Lett 40:4453

    Article  CAS  Google Scholar 

  79. Bohé L, Kammoun M (2002) Tetrahedron Lett 43:803

    Article  Google Scholar 

  80. Page PCB, Rassias GA, Bethell D, Schilling MB (1998) J Org Chem 63:2774

    Article  CAS  Google Scholar 

  81. Page PCB, Rassias GA, Barros D, Bethell D, Schilling MB (2000) J Chem Soc Perkin Trans 1:3325

    Article  Google Scholar 

  82. Rieche A, Schmitz E (1956) Chem Ber 89:1254

    Article  CAS  Google Scholar 

  83. Page PCB, Rassias GA, Barros D, Ardakani A, Buckley B, Bethell D, Smith TAD, Slawin AMZ (2001) J Org Chem 66:6926

    Article  CAS  Google Scholar 

  84. Page PCB, Rassias GA, Barros D, Ardakani A, Bethell D, Merifield E (2002) Synlett 580

    Google Scholar 

  85. Vachon J, Rentsch S, Martinez A, Marsol C, Lacour J (2007) Org Biomol Chem 5:501

    Article  CAS  Google Scholar 

  86. Page PCB, Buckley BR, Blacker AJ (2004) Org Lett 6:1543

    Article  Google Scholar 

  87. Page PCB, Parker P, Rassias GA, Buckley BR, Bethell D (2008) Adv Synth Catal 350:1867

    Article  CAS  Google Scholar 

  88. Page PCB, Marken F, Williamson C, Chan Y, Buckley BR, Bethell D (2008) Adv Synth Catal 350:1149

    Article  CAS  Google Scholar 

  89. Page PCB, Barros D, Buckley BR, Ardakani A, Marples BA (2004) J Org Chem 69:3595

    Article  CAS  Google Scholar 

  90. Page PCB, Barros D, Buckley BR, Blacker AJ, Marples BA (2005) Tetrahedron: Asymm 16:3488

    Article  Google Scholar 

  91. Page PCB, Buckley BR, Heaney H, Blacker AJ (2005) Org Lett 7:375

    Article  Google Scholar 

  92. Page PCB, Appleby LF, Day D, Chan Y, Buckley BR, Allin SM, McKenzie MJ (2009) Org Lett 11:1991

    Article  Google Scholar 

  93. Maringo M, Franzén J, Poulsen TB, Zhuang W, Jørgensen KA (2005) J Am Chem Soc 127:6964

    Article  Google Scholar 

  94. Lee S, MacMillan DWC (2006) Tetrahedron 62:11413

    Article  CAS  Google Scholar 

  95. Russo A, Lattanzi A (2008) Eur J Org Chem 2767

    Google Scholar 

  96. (a) Aggarwal VK, Lopin C, Sandrinelli FJ (2003) J Am Chem Soc 125:7596; (b) Adamo MFA, Aggarwal VK, Sage MA (2000) J Am Chem Soc 122:8317

    Google Scholar 

  97. Ho C-Y, Chen Y-C, Wong M-K, Yang D (2005) J Org Chem 70:898

    Article  CAS  Google Scholar 

  98. For a mini review see: Armstrong A (2004) Angew Chem Int Ed 43:1460

    Google Scholar 

  99. Goncalves MH, Martinez A, Grass S, Page PCB, Lacour J (2006) Tetrahedron Lett 47:5297

    Article  CAS  Google Scholar 

  100. Page PCB, Farah MM, Buckley BR, Blacker AJ, Lacour J (2008) Synlett 1381

    Google Scholar 

  101. Lu X, Liu Y, Sun B, Cindric B, Deng L (2008) J Am Chem Soc 130:8134

    Article  CAS  Google Scholar 

  102. Wang X, Reisinger CM, List B (2008) J Am Chem Soc 130:6070

    Article  CAS  Google Scholar 

  103. Reisinger CM, Wang X, List B (2008) Angew Chem Int Ed 47:1119

    Article  Google Scholar 

  104. Wang X, List B (2008) Angew Chem Int Ed 47:8112

    Article  Google Scholar 

  105. Andersen KK, Goffield W, Papankolaou NE, Foley JW, Perkins RI (1964) J Am Chem Soc 86:5637

    Article  CAS  Google Scholar 

  106. Ruano JLC, Aranda MT, Zarzuelo MM (2003) Org Lett 5:75

    Article  Google Scholar 

  107. Zhengzu H, Krishnamurthy D, Grover P, Wilkinson HS, Fang QC, Su XP, Lu ZH, Magiera D, Senanayake CH (2003) Angew Chem Int Ed 42:2032

    Article  Google Scholar 

  108. Kagan HB, Pitchen P (1984) Tetrahedron Lett 25:1049

    Article  Google Scholar 

  109. Bolm C, Bienewald F (1995) Angew Chem Int Ed 34:2640

    CAS  Google Scholar 

  110. Russo A, Lattanzi A (2009) Adv Synth Catal 351:521

    Article  CAS  Google Scholar 

  111. Habibi D, Zolfigol MA, Safaiee M, Shamsian A, Ghorbani-Choghamarani A (2009) Catal Commun 10:1257

    Article  CAS  Google Scholar 

  112. (a) Damavandi JA, Karami B, Zolfigol MA (2002) Synlett 933; (b) Zolfigol MA, Amani K, Ghorbani-Choghamarani A, Hajjami M, Ayazi-Nasrabadi R, Jafari S (2009) Catal Commun 9:1739

    Google Scholar 

  113. Davis FA, Billmers J (1983) J Org Chem 48:2672

    Article  CAS  Google Scholar 

  114. Davis FA, Jenkins RH, Awad SB, Stringer OD, Watson WH, Galley J (1982) J Am Chem Soc 104:5412

    Article  CAS  Google Scholar 

  115. Davis FA, McCauley JP, Chattopachyay S, Harakal ME, Towson JC, Watson WH, Tavabaiepour J (1987) J Am Chem Soc 109:3370

    Article  CAS  Google Scholar 

  116. Davis FA, Jewson JC, Weismiller MC, Lal S, Caroll PC (1988) J Am Chem Soc 110:8477

    Article  CAS  Google Scholar 

  117. Boyd DR, Malone JF, McGuckin MR, Jennings WB, Rutherford M, Saket BM (1994) J Chem Soc Perkin Trans II 1145

    Google Scholar 

  118. Jennings WB, Kochanewycz MJ, Lovely CJ, Boyd DR (1994) J Chem Soc Chem Commun 2569

    Google Scholar 

  119. Hanquet G, Lusinchi X, Milliet P (1988) Tetrahedron Lett 29:2817

    Article  CAS  Google Scholar 

  120. Desmarteau DD, Petrov VA, Montanari V, Preynolato M, Resnati G (1994) J Org Chem 59:5762

    Article  Google Scholar 

  121. Page PCB, Bethell D, Heer JP, Collington EW, Andrews DM (1995) Synlett 773

    Google Scholar 

  122. (a) Page PCB, Graham AE, Bethell D, Park BK (1993) Synth Commun 23:1507; (b) Page PCB, Bethell D, Heer JP, Collington EW, Andrews DM (1994) Tetrahedron Lett 35:9629; (c) Page PCB, Heer JP, Bethell D, Collington EW, Andrews D (1995) Synlett 773

    Google Scholar 

  123. Andrews DM, Bethell D, Collington EW, Heer JP, Page PCB (1995) Tetrahedron: Asymm 6:2911

    Article  Google Scholar 

  124. Page PCB, Bethell D, Stocks PA, Heer JP, Graham AE, Vahedi H, Healy M, Collington EW, Andrews DM (1997) Synlett 1355

    Google Scholar 

  125. Page PCB, Bethell D, Vahedi H (2000) J Org Chem 65:6756

    Article  Google Scholar 

  126. Bach RD, Coddens BA, McDouall JW, Shegal BS (1990) J Org Chem 55:3325

    Article  CAS  Google Scholar 

  127. Gluszynska A, Maćkowska I, Rozwadowska MD, Sienniak W (2004) Tetrahedron: Asymm 15:2499

    Article  CAS  Google Scholar 

  128. Del Rio RE, Wang B, Achab S, Bohé L (2007) Org Lett 9:2265

    Article  Google Scholar 

  129. (a) Ojima I (ed.) (2000) Catalytic asymmetric synthesis, 2nd edn. Chaps. 1–3. Wiley VCH, New York; (b) Zhang X (ed.) (2004) Tetrahedron:Asymm 15:2099; (c) Crepy KVL, Imamoto T (2003) Top Curr Chem 1

    Google Scholar 

  130. (a) Seayad J, List B (2005) Org Biomol Chem 3:719; (b) Connon SJ (2006) Angew Chem Int Ed 45:3909

    Google Scholar 

  131. (a) Pietrusiewicz KM, Zablocka M (1994) Chem Rev 94:1375; (b) Grabulosa A, Granell J, Muller G (2007) Coord Chem Rev 251:25

    Google Scholar 

  132. Bergin E, O’Connor CT, Robinson SB, McGarrigle EM, O’Mahony CP, Gilheany DG (2007) J Am Chem Soc 129:9566

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Loughborough University, Loughborough, Leicestershire, LE11 5EE, UK

    Benjamin R. Buckley & Stephen P. Neary

Authors
  1. Benjamin R. Buckley
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Stephen P. Neary
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Benjamin R. Buckley .

Editor information

Editors and Affiliations

  1. Department of Chemistry, Humboldt University Berlin, Brook-Taylor-Str. 2, Berlin, 12489, Berlin, Germany

    Rainer Mahrwald

Rights and permissions

Reprints and permissions

Copyright information

© 2011 Springer Science+Business Media B.V.

About this chapter

Cite this chapter

Buckley, B.R., Neary, S.P. (2011). Organocatalysed Asymmetric Oxidation Reactions. In: Mahrwald, R. (eds) Enantioselective Organocatalyzed Reactions I. Springer, Dordrecht. https://doi.org/10.1007/978-90-481-3865-4_1

Download citation

Publish with us

Policies and ethics

Search

Navigation