Skip to main content

Chiral Ketone and Iminium Catalysts for Olefin Epoxidation

  • Chapter
  • First Online:
Asymmetric Organocatalysis

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 291))

  • 4975 Accesses

Abstract

Organo-catalyzed asymmetric epoxidation has received much attention in the past 30 years and significant progress has been made for various types of olefins. This review will cover the advancement made in the field of chiral ketone and chiral iminium salt-catalyzed epoxidations.

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

Access this chapter

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. Besse P, Veschambre H (1994) Tetrahedron 50:8885

    Article  CAS  Google Scholar 

  2. Bonini C, Righi G (2002) Tetrahedron 58:4981

    Article  CAS  Google Scholar 

  3. Katsuki T, Martin VS (1996) Org React 48:1

    CAS  Google Scholar 

  4. Johnson RA, Sharpless KB (2000) In: Ojima I (ed) Catalytic asymmetric synthesis, 2nd edn. Wiley-VCH, New York, Chap. 6A

    Google Scholar 

  5. Jacobsen EN (1993) In: Ojima I (ed) Catalytic asymmetric synthesis, 1st edn. Wiley-VCH, New York, Chap. 4.2

    Google Scholar 

  6. Collman JP, Zhang X, Lee VJ, Uffelman ES, Brauman JI (1993) Science 261:1404

    Article  CAS  Google Scholar 

  7. Mukaiyama T (1996) Aldrichim Acta 1996 29:59

    CAS  Google Scholar 

  8. Katsuki T (2000) In: Ojima I (ed) Catalytic asymmetric synthesis, 2nd edn. Wiley-VCH, New York, Chap. 6B

    Google Scholar 

  9. McGarrigle EM, Gilheany DG (2005) Chem Rev 105:1563

    Article  CAS  Google Scholar 

  10. Xia QH, Ge HQ, Ye CP, Liu ZM, Su KX (2005) Chem Rev 105:1603

    Article  CAS  Google Scholar 

  11. Porter MJ, Skidmore J (2000) Chem Commun 2000:1215

    Article  Google Scholar 

  12. Lauret C, Roberts SM (2002) Aldrichim Acta 35:47

    CAS  Google Scholar 

  13. Kelly DR, Roberts SM (2006) Biopolymers 84:74

    Article  CAS  Google Scholar 

  14. Shibasaki M, Kanai M, Matsunaga S (2006) Aldrichim Acta 39:31

    CAS  Google Scholar 

  15. Murray RW (1989) Chem Rev 89:1187

    Article  CAS  Google Scholar 

  16. Adam W, Curci R, Edwards JO (1989) Acc Chem Res 22:205

    Article  CAS  Google Scholar 

  17. Curci R, Dinoi A, Rubino MF (1995) Pure Appl Chem 67:811

    Article  CAS  Google Scholar 

  18. Adam W, Smerz AK (1996) Bull Soc Chim Belg 105:581

    CAS  Google Scholar 

  19. Adam W, Saha-Möller CR, Ganeshpure PA (2001) Chem Rev 101:3499

    Article  CAS  Google Scholar 

  20. Adam W, Saha-Möller CR, Zhao C-G (2002) Org React 61:219

    CAS  Google Scholar 

  21. Wong OA, Shi Y (2008) Chem Rev 108:3958

    Article  CAS  Google Scholar 

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

    Google Scholar 

  23. Frohn M, Shi Y (2000) Synthesis 1979

    Google Scholar 

  24. Shi Y (2002) J Synth Org Chem Jpn 60:342

    Article  CAS  Google Scholar 

  25. Shi Y (2004) In: Bäckvall JE (ed) Modern oxidation methods, 1st edn. Wiley-VCH, Weinheim, Chap. 3

    Google Scholar 

  26. Shi Y (2004) Acc Chem Res 37:488

    Article  CAS  Google Scholar 

  27. Yang D (2004) Acc Chem Res 37:497

    Article  CAS  Google Scholar 

  28. Shi Y (2006) In: Ager D (ed) Handbook of chiral chemicals, 2nd edn. CRC, Taylor & Francis Group, Boca Raton, Chap. 10

    Google Scholar 

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

    Google Scholar 

  30. Curci R, D’Accolti L, Fiorentino M, Rosa A (1995) Tetrahedron Lett 36:5831

    CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  32. Yang D, Yip YC, Tang MW, Wong MK, Zheng JH, Cheung KK (1996) J Am Chem Soc 118:491

    Article  CAS  Google Scholar 

  33. Yang D, Wang XC, Wong MK, Yip YC, Tang MW (1996) J Am Chem Soc 118:11311

    Article  CAS  Google Scholar 

  34. Yang D, Wong MK, Yip YC, Wang XC, Tang MW, Zheng JH, Cheung KK (1998) J Am Chem Soc 120:5943

    Article  CAS  Google Scholar 

  35. Seki M, Furutani T, Imashiro R, Kuroda T, Yamanaka T, Harada N, Arakawa H, Musama M, Hashiyama T (2001) Tetrahedron Lett 42:8201

    Article  CAS  Google Scholar 

  36. Imashiro R, Seki M (2004) J Org Chem 69:4216

    Article  CAS  Google Scholar 

  37. Song CE, Kim YH, Lee KC, Lee Sg, Jin BW (1997) Tetrahedron: Asymmetry 8:2921

    Article  CAS  Google Scholar 

  38. Kim YH, Lee KC, Chi DY, Lee Sg, Song CE (1999) Bull Korean Chem Soc 20:831

    CAS  Google Scholar 

  39. Adam W, Zhao CG (1997) Tetrahedron: Asymmetry 8:3995

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  41. Stearman CJ, Behar V (2002) Tetrahedron Lett 43:1943

    Article  CAS  Google Scholar 

  42. Matsumoto K, Tomioka K (2001) Heterocycles 54:615

    Article  CAS  Google Scholar 

  43. Matsumoto K, Tomioka K (2002) Tetrahedron Lett 43:631

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  45. Denmark SE, Wu Z (1997) J Org Chem 62:8964

    Article  CAS  Google Scholar 

  46. Denmark SE, Wu Z, Crudden CM, Matsuhashi H (1997) J Org Chem 62:8288

    Article  CAS  Google Scholar 

  47. Denmark SE, Wu Z (1998) J Org Chem 63:2810

    Article  CAS  Google Scholar 

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

    Google Scholar 

  49. Armstrong A, Ahmed G, Dominguez-Fernandez B, Hayter BR, Wailes JS (2002) J Org Chem 67:8610

    Article  CAS  Google Scholar 

  50. Armstrong A, Hayter BR, Moss WO, Reeves JR, Wailes JS (2000) Tetrahedron Asymmetry 11:2057

    Article  CAS  Google Scholar 

  51. Armstrong A, Moss WO, Reeves JR (2001) Tetrahedron Asymmetry 12:2779

    Article  CAS  Google Scholar 

  52. Armstrong A, Tsuchiya T (2006) Tetrahedron 62:257

    Article  CAS  Google Scholar 

  53. Tu Y, Wang ZX, Shi Y (1996) J Am Chem Soc 118:9806

    Article  CAS  Google Scholar 

  54. Wang ZX, Tu Y, Frohn M, Zhang JR, Shi Y (1997) J Am Chem Soc 119:11224

    Article  CAS  Google Scholar 

  55. Mio S, Kumagawa Y, Sugai S (1991) Tetrahedron 47:2133

    Article  CAS  Google Scholar 

  56. Tu Y, Frohn M, Wang ZX, Shi Y (2003) Org Synth 80:1

    CAS  Google Scholar 

  57. Chen CC, Whistler RL (1988) Carbohydr Res 175:265

    Article  CAS  Google Scholar 

  58. Zhao MX, Shi Y (2006) J Org Chem 71:5377

    Article  CAS  Google Scholar 

  59. Ball DL, Edwards JO (1956) J Am Chem Soc 78:1125

    Article  CAS  Google Scholar 

  60. Montgomery RE (1974) J Am Chem Soc 96:7820

    Article  CAS  Google Scholar 

  61. Wang ZX, Tu Y, Frohn M, Shi Y (1997) J Org Chem 62:2328

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  63. Wang ZX, Shi Y (1998) J Org Chem 63:3099

    Article  CAS  Google Scholar 

  64. Frohn M, Dalkiewicz M, Tu Y, Wang ZX, Shi Y (1998) J Org Chem 63:2948

    Article  CAS  Google Scholar 

  65. Cao GA, Wang ZX, Tu Y, Shi Y (1998) Tetrahedron Lett 39:4425

    Article  CAS  Google Scholar 

  66. Wang ZX, Cao GA, Shi Y (1999) J Org Chem 64:7646

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  68. Zhu Y, Manske KJ, Shi Y (1999) J Am Chem Soc 121:4080

    Article  CAS  Google Scholar 

  69. Feng X, Shu L, Shi Y (1999) J Am Chem Soc 121:11002

    Article  CAS  Google Scholar 

  70. Zhu Y, Shu L, Tu Y, Shi Y (2001) J Org Chem 66:1818

    Article  CAS  Google Scholar 

  71. Tian H, She X, Shi Y (2001) Org Lett 3:715

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  74. Shu L, Shi Y (2001) Tetrahedron 57:5231

    Article  Google Scholar 

  75. Wang ZX, Shu L, Frohn M, Tu Y, Shi Y (2003) Org Synth 80:9

    CAS  Google Scholar 

  76. Curci R, Dinoi A, Rubino MF (1995) Pure Appl Chem 67:811

    Article  CAS  Google Scholar 

  77. Adam W, Smerz AK (1996) Bull Soc Chim Belg 105:581

    CAS  Google Scholar 

  78. Armstrong A, Washington I, Houk KN (2000) J Am Chem Soc 122:6297

    Article  CAS  Google Scholar 

  79. Baumstark AL, McCloskey CJ (1987) Tetrahedron Lett 28:3311

    Article  CAS  Google Scholar 

  80. Baumstark AL, Vasquez PC (1988) J Org Chem 53:3437

    Article  CAS  Google Scholar 

  81. Bach RD, Andrés JL, Owensby AL, Schlegel HB, McDouall JJW (1992) J Am Chem Soc 114:7207

    Article  CAS  Google Scholar 

  82. Houk KN, Liu J, DeMello NC, Condroski KR (1997) J Am Chem Soc 119:10147

    Article  CAS  Google Scholar 

  83. Jenson C, Liu J, Houk KN, Jorgensen WL (1997) J Am Chem Soc 119:12982

    Article  CAS  Google Scholar 

  84. Deubel DV (2001) J Org Chem 66:3790

    Article  CAS  Google Scholar 

  85. Singleton DA, Wang Z (2005) J Am Chem Soc 127:6679

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  87. Lorenz JC, Frohn M, Zhou X, Zhang JR, Tang Y, Burke C, Shi Y (2005) J Org Chem 70:2904

    Article  CAS  Google Scholar 

  88. Bian J, Van Wingerden M, Ready JM (2006) J Am Chem Soc 128:7428

    Article  CAS  Google Scholar 

  89. Tong R, Valentine JC, McDonald FE, Cao R, Fang X, Hardcastle KI (2007) J Am Chem Soc 129:1050

    Article  CAS  Google Scholar 

  90. Xiong Z, Corey EJ (2000) J Am Chem Soc 122:4831

    Article  CAS  Google Scholar 

  91. Xiong Z, Corey EJ (2000) J Am Chem Soc 122:9328

    Article  CAS  Google Scholar 

  92. McDonald FE, Wang X, Do B, Hardcastle KI (2000) Org Lett 2:2917

    Article  CAS  Google Scholar 

  93. McDonald FE, Bravo F, Wang X, Wei X, Toganoh M, Rodríguez JR, Do B, Neiwert WA, Hardcastle KI (2002) J Org Chem 67:2515

    Article  CAS  Google Scholar 

  94. Bravo F, McDonald FE, Neiwert WA, Do B, Hardcastle KI (2003) Org Lett 5:2123

    Article  CAS  Google Scholar 

  95. Valentine JC, McDonald FE, Neiwert WA, Hardcastle KI (2005) J Am Chem Soc 127:4586

    Article  CAS  Google Scholar 

  96. Vilotijevic I, Jamison TF (2007) Science 317:1189

    Article  CAS  Google Scholar 

  97. Tian H, She X, Shu L, Yu H, Shi Y (2000) J Am Chem Soc 122:11551

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  100. Shu L, Shen YM, Burke C, Goeddel D, Shi Y (2003) J Org Chem 68:4963

    Article  CAS  Google Scholar 

  101. Hickey M, Goeddel D, Crane Z, Shi Y (2004) Proc Natl Acad Sci USA 101:5794

    Article  CAS  Google Scholar 

  102. Shu L, Wang P, Gan Y, Shi Y (2003) Org Lett 5:293

    Article  CAS  Google Scholar 

  103. Goeddel D, Shu L, Yuan Y, Wong OA, Wang B, Shi Y (2006) J Org Chem 71:1715

    Article  CAS  Google Scholar 

  104. Zhao MX, Goeddel D, Li K, Shi Y (2006) Tetrahedron 62:8064

    Article  CAS  Google Scholar 

  105. Shu L, Shi Y (2004) Tetrahedron Lett 45:8115

    Article  CAS  Google Scholar 

  106. Wong OA, Shi Y (2006) J Org Chem 71:3973

    Article  CAS  Google Scholar 

  107. Burke CP, Shi Y (2006) Angew Chem Int Ed 45:4475

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  109. Shen YM, Wang B, Shi Y (2006) Angew Chem Int Ed 45:1429

    Article  CAS  Google Scholar 

  110. Shen YM, Wang B, Shi Y (2006) Tetrahedron Lett 47:5455

    Article  CAS  Google Scholar 

  111. Wang B, Shen YM, Shi Y (2006) J Org Chem 71:9519

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  113. Shing TKM, Leung GYC, Yeung KW (2003) Tetrahedron Lett 44:9225

    Article  CAS  Google Scholar 

  114. Shing TKM, Leung GYC, Luk T (2005) J Org Chem 70:7279

    Article  CAS  Google Scholar 

  115. Shing TKM, Luk T, Lee CM (2006) Tetrahedron 62:6621

    Article  CAS  Google Scholar 

  116. Bez G, Zhao CG (2003) Tetrahedron Lett 44:7403

    Article  CAS  Google Scholar 

  117. Wang ZX, Shi Y (1997) J Org Chem 62:8622

    Article  CAS  Google Scholar 

  118. Wang ZX, Miller SM, Anderson OP, Shi Y (1999) J Org Chem 64:6443

    Article  CAS  Google Scholar 

  119. Yang D, Yip YC, Chen J, Cheung KK (1998) J Am Chem Soc 120:7659

    Article  CAS  Google Scholar 

  120. Solladié-Cavallo A, Jierry L, Bouérat L, Taillasson P (2001) Tetrahedron: Asymmetry 12:883

    Article  Google Scholar 

  121. Solladié-Cavallo A, Bouérat L, Jierry L (2001) Eur J Org Chem 4557

    Google Scholar 

  122. Solladié-Cavallo A, Jierry L, Klein A (2003) C R Chimie 6:603

    Article  CAS  Google Scholar 

  123. Solladié-Cavallo A, Bouérat L (2000) Org Lett 2:3531

    Article  CAS  Google Scholar 

  124. Solladié-Cavallo A, Jierry L, Norouzi-Arasi H, Tahmassebi D (2004) J Fluorine Chem 125:1371

    Article  CAS  Google Scholar 

  125. Solladié-Cavallo A, Jierry L, Lupattelli P, Bovicelli P, Antonioletti R (2004) Tetrahedron 60:11375

    Article  CAS  Google Scholar 

  126. Solladié-Cavallo A, Jierry L, Klein A, Schmitt M, Welter R (2004) Tetrahedron: Asymmetry 15:3891

    Article  CAS  Google Scholar 

  127. Bortolini O, Fantin G, Fogagnolo M, Mari L (2006) Tetrahedron 62:4482

    Article  CAS  Google Scholar 

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

    Article  Google Scholar 

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

    Article  Google Scholar 

  130. Milliet P, Picot A, Lusinchi X (1981) Tetrahedron 37:4201

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  132. Hanquet G, Lusinchi X, Milliet P (1993) Tetrahedron 49:423

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

  134. Hanquet G, Lusinchi X, Milliet P (1991) CR Acad Sci Paris t 313 Série II, p 625

    Google Scholar 

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

    Article  CAS  Google Scholar 

  136. Bohé L, Hanquet G, Lusinchi M, Lusinchi X (1993) Tetrahedron Lett 34:7271

    Article  Google Scholar 

  137. Bohé L, Lusinchi M, Lusinchi X (1999) Tetrahedron 55:141

    Article  Google Scholar 

  138. Brózda D, Koroniak Ł, Rozwadowska MD (2000) Tetrahedron Asymmetry 11:3017

    Article  Google Scholar 

  139. Głuszyńska A, Maćkowska I, Rozwadowska MD, Sienniak W (2004) Tetrahedron Asymmetry 15:2499

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  Google Scholar 

  142. 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 

  143. Page PCB, Buckley BR, Rassias GA, Blacker AJ (2006) Eur J Org Chem 803

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  146. Page PCB, Buckley BR, Barros D, Blacker AJ, Heaney H, Marples BA (2006) Tetrahedron 62:6607

    Article  CAS  Google Scholar 

  147. Aggarwal VK, Wang MF (1996) Chem Commun 191

    Google Scholar 

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

    Article  CAS  Google Scholar 

  149. Page PCB, Buckley BR, Blacker AJ (2006) Org Lett 8:4669

    Article  CAS  Google Scholar 

  150. Page PCB, Buckley BR, Barros D, Blacker AJ, Marples BA, Elsegood MRJ (2007) Tetrahedron 63:5386

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  152. Page PCB, Farah MM, Buckley BR, Blacker AJ (2007) J Org Chem 72:4424

    Article  CAS  Google Scholar 

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

    Google Scholar 

  154. Lacour J, Monchaud D, Marsol C (2002) Tetrahedron Lett 43:8257

    Article  CAS  Google Scholar 

  155. Vachon J, Pérollier C, Monchaud D, Marsol C, Ditrich K, Lacour J (2005) J Org Chem 70:5903

    Article  CAS  Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

  159. Wong MK, Ho LM, Zheng YS, Ho CY, Yang D (2001) Org Lett 3:2587

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Yian Shi .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2010 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Wong, O.A., Shi, Y. (2010). Chiral Ketone and Iminium Catalysts for Olefin Epoxidation. In: List, B. (eds) Asymmetric Organocatalysis. Topics in Current Chemistry, vol 291. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-02815-1_16

Download citation

Publish with us

Policies and ethics