Skip to main content

Bifunctional Acid Catalysts for Organic Synthesis

  • Chapter
  • First Online:
Bifunctional Molecular Catalysis

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 37))

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 169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
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. Yamamoto H, Futatsugi K (2005) Angew Chem Int Ed 44:1924

    Article  CAS  Google Scholar 

  2. Yamamoto H, Futatsugi K (2008) Recent advance of “combined acid” strategy for asymmetric catalysis. In: Yamamoto H, Ishihara K (eds) Acid catalysis in modern organic synthesis. Wiley-VCH, Weinheim

    Google Scholar 

  3. Jacobsen EN, Pfaltz A, Yamamoto H (eds) (1999) Comprehensive asymmetric catalysis. Springer, Berlin

    Google Scholar 

  4. Ojima I (ed) (2010) Catalytic asymmetric synthesis, 3rd edn. Wiley, Hoboken

    Google Scholar 

  5. Yamamoto H (ed) (1999) Lewis acid reagents: a practical approach. Oxford University Press, Oxford

    Google Scholar 

  6. Yamamoto H (ed) (2000) Lewis acids in organic synthesis. Wiley-VCH, Weinheim

    Google Scholar 

  7. Yamamoto H, Ishihara K (eds) (2008) Acid catalysis in modern organic synthesis. Wiley-VCH, Weinheim

    Google Scholar 

  8. Yoon TP, Jacobsen EN (2003) Science 299:1691

    Article  CAS  Google Scholar 

  9. Wang C, Xi Z (2007) Chem Soc Rev 36:1395

    Article  CAS  Google Scholar 

  10. Zhong C, Shi X (2010) European J Org Chem 2999

    Google Scholar 

  11. Hirao A, Itsuno S, Nakahama S, Yamazaki N (1981) J Chem Soc Chem Commun 315

    Google Scholar 

  12. Itsuno S, Hirao A, Nakahama S, Yamazaki N (1983) J Chem Soc Perkin Trans 1 1673

    Google Scholar 

  13. Itsuno S, Ito K, Hirao A, Nakahama S (1983) J Chem Soc Chem Commun 469

    Google Scholar 

  14. Itsuno S, Nakano M, Miyazaki K, Masuda H, Ito K, Hirao A, Nakahama S (1985) J Chem Soc Perkin Trans 1 2039

    Google Scholar 

  15. Corey EJ, Bakshi RK, Shibata S (1987) J Am Chem Soc 109:5551

    Article  CAS  Google Scholar 

  16. Corey EJ, Bakshi RK, Shibata S, Chen C-P, Singh VK (1987) J Am Chem Soc 109:7925

    Article  CAS  Google Scholar 

  17. Corey EJ, Shibata S, Bakshi RK (1988) J Org Chem 53:2861

    Article  CAS  Google Scholar 

  18. Corey EJ (1990) Pure Appl Chem 62:1209

    Article  CAS  Google Scholar 

  19. Corey EJ, Helal CJ (1998) Angew Chem Int Ed 37:1986

    Article  CAS  Google Scholar 

  20. Corey EJ, Loh T-P (1991) J Am Chem Soc 113:8966

    Article  CAS  Google Scholar 

  21. Corey EJ, Shibata T, Lee TW (2002) J Am Chem Soc 124:3808

    Article  CAS  Google Scholar 

  22. Corey EJ (2009) Angew Chem Int Ed 48:2100

    Article  CAS  Google Scholar 

  23. Ryu DH, Lee TW, Corey EJ (2002) J Am Chem Soc 124:9992

    Article  CAS  Google Scholar 

  24. Ryu DH, Corey EJ (2003) J Am Chem Soc 125:6388

    Article  CAS  Google Scholar 

  25. Ryu DH, Zhou G, Corey EJ (2004) J Am Chem Soc 126:4800

    Article  CAS  Google Scholar 

  26. Zhou G, Hu Q-Y, Corey EJ (2003) Org Lett 5:3979

    Article  CAS  Google Scholar 

  27. Balskus EP, Jacobsen EN (2007) Science 317:1736

    Article  CAS  Google Scholar 

  28. Ryu DH, Corey EJ (2004) J Am Chem Soc 126:8106

    Article  CAS  Google Scholar 

  29. Ryu DH, Corey EJ (2005) J Am Chem Soc 127:5384

    Article  CAS  Google Scholar 

  30. Gnanadesikan V, Corey EJ (2006) Org Lett 8:4943

    Article  CAS  Google Scholar 

  31. Liu D, Hong S, Corey EJ (2006) J Am Chem Soc 128:8160

    Article  CAS  Google Scholar 

  32. Corey EJ, Rhode JJ (1997) Tetrahedron Lett 38:37

    Article  CAS  Google Scholar 

  33. Corey EJ, Lee TW (2001) Chem Commun 1321

    Google Scholar 

  34. Paddon-Row MN, Anderson CD, Houk KN (2009) J Org Chem 74:861

    Article  CAS  Google Scholar 

  35. Hu Q-Y, Rege PD, Corey EJ (2004) J Am Chem Soc 126:5984

    Article  CAS  Google Scholar 

  36. Yeung Y-Y, Chein R-J, Corey EJ (2007) J Am Chem Soc 129:10346

    Article  CAS  Google Scholar 

  37. Yeung Y-Y, Hong S, Corey EJ (2006) J Am Chem Soc 128:6310

    Article  CAS  Google Scholar 

  38. Snyder SA, Corey EJ (2006) J Am Chem Soc 128:740

    Article  CAS  Google Scholar 

  39. Zhou G, Corey EJ (2005) J Am Chem Soc 127:11958

    Article  CAS  Google Scholar 

  40. Mukherjee S, Scopton AP, Corey EJ (2010) Org Lett 12:1836

    Article  CAS  Google Scholar 

  41. Hu Q-Y, Zhou G, Corey EJ (2004) J Am Chem Soc 126:13708

    Article  CAS  Google Scholar 

  42. Canales E, Corey EJ (2008) Org Lett 10:3271

    Article  CAS  Google Scholar 

  43. Futatsugi K, Yamamoto H (2005) Angew Chem Int Ed 44:1484

    Article  CAS  Google Scholar 

  44. Liu D, Canales E, Corey EJ (2007) J Am Chem Soc 129:1498

    Article  CAS  Google Scholar 

  45. Canales E, Corey EJ (2007) J Am Chem Soc 129:12686

    Article  CAS  Google Scholar 

  46. Li P, Payette JN, Yamamoto H (2007) J Am Chem Soc 129:9534

    Article  CAS  Google Scholar 

  47. Payette JN, Yamamoto H (2007) J Am Chem Soc 129:9536

    Article  CAS  Google Scholar 

  48. Payette JN, Yamamoto H (2009) Angew Chem Int Ed 48:8060

    Article  CAS  Google Scholar 

  49. Paddon-Row MN, Kwan LCH, Willis AC, Sherburn MS (2008) Angew Chem Int Ed 47:7013

    Article  CAS  Google Scholar 

  50. Maruoka K, Itoh T, Shirasaka T, Yamamoto H (1988) J Am Chem Soc 110:310

    Article  CAS  Google Scholar 

  51. Ishihara K, Kobayashi J, Inanaga K, Yamamoto H (2001) Synlett 394

    Google Scholar 

  52. Li P, Yamamoto H (2010) Chem Commun. doi:10.1039/c0cc01619e

    Google Scholar 

  53. Li P, Yamamoto H (2009) J Am Chem Soc 131:16628

    Article  CAS  Google Scholar 

  54. Ishihara K, Kaneeda M, Yamamoto H (1994) J Am Chem Soc 116:11179

    Article  CAS  Google Scholar 

  55. Ishihara K, Nakashima D, Hiraiwa Y, Yamamoto H (2003) J Am Chem Soc 125:24

    Article  CAS  Google Scholar 

  56. Cheon CH, Yamamoto H (2008) J Am Chem Soc 130:9246

    Article  CAS  Google Scholar 

  57. Lou S, Moquist PN, Schaus SE (2006) J Am Chem Soc 128:12660

    Article  CAS  Google Scholar 

  58. Barnett DS, Moquist PN, Schaus SE (2009) Angew Chem Int Ed 48:8679

    Article  CAS  Google Scholar 

  59. Lou S, Moquist PN, Schaus SE (2007) J Am Chem Soc 129:15398

    Article  CAS  Google Scholar 

  60. Lou S, Schaus SE (2008) J Am Chem Soc 130:6922

    Article  CAS  Google Scholar 

  61. Bishop JA, Lou S, Schaus SE (2009) Angew Chem Int Ed 48:4337

    Article  CAS  Google Scholar 

  62. Akiyama T, Itoh J, Yokota K, Fuchibe K (2004) Angew Chem Int Ed 43:1566

    Article  CAS  Google Scholar 

  63. Uraguchi D, Terada M (2004) J Am Chem Soc 126:5356

    Article  CAS  Google Scholar 

  64. Akiyama T (2007) Chem Rev 107:5744

    Article  CAS  Google Scholar 

  65. Terada M (2008) Chem Commun 4097

    Google Scholar 

  66. Terada M (2010) Bull Chem Soc Jpn 83:101

    Article  CAS  Google Scholar 

  67. Nakashima D, Yamamoto H (2006) J Am Chem Soc 128:9626

    Article  CAS  Google Scholar 

  68. Jiao P, Nakashima D, Yamamoto H (2008) Angew Chem Int Ed 47:2411

    Article  CAS  Google Scholar 

  69. Cheon CH, Yamamoto H (2010) Org Lett 12:2476

    Article  CAS  Google Scholar 

  70. Yang L, Zhu Q, Guo S, Qian B, Xia C, Huang H (2010) Chem Eur J 16:1638

    Article  CAS  Google Scholar 

  71. Lv J, Li X, Zhong L, Luo S, Cheng J-P (2010) Org Lett 12:1096

    Article  CAS  Google Scholar 

  72. Taylor MS, Jacobsen EN (2006) Angew Chem Int Ed 45:1520

    Article  CAS  Google Scholar 

  73. Doyle AG, Jacobsen EN (2007) Chem Rev 107:5713

    Article  CAS  Google Scholar 

  74. Shi Y-L, Shi M (2007) Adv Synth Catal 349:2129

    Article  CAS  Google Scholar 

  75. Weil T, Kotke M, Kleiner CM, Schreiner PR (2008) Org Lett 8:1513

    Article  Google Scholar 

  76. Klausen RS, Jacobsen EN (2009) Org Lett 11:887

    Article  CAS  Google Scholar 

  77. Xu H, Zuend SJ, Woll MG, Tao Y, Jacobsen EN (2010) Science 327:986

    Article  CAS  Google Scholar 

  78. Knowles RR, Lin S, Jacobsen EN (2010) J Am Chem Soc 132:5030

    Article  CAS  Google Scholar 

  79. Taylor MS, Jacobsen EN (2004) J Am Chem Soc 126:10558

    Article  CAS  Google Scholar 

  80. Taylor MS, Tokunaga N, Jacobsen EN (2005) Angew Chem Int Ed 41:6700

    Article  Google Scholar 

  81. Raheem IT, Thiara PS, Peterson EA, Jacobsen EN (2007) J Am Chem Soc 129:13404

    Article  CAS  Google Scholar 

  82. Raheem IT, Thiara PS, Jacobsen EN (2008) Org Lett 10:1577

    Article  CAS  Google Scholar 

  83. Reisman SE, Doyle AG, Jacobsen EN (2008) J Am Chem Soc 130:7198

    Article  CAS  Google Scholar 

  84. De CK, Klauber EG, Seidel D (2009) J Am Chem Soc 131:17060

    Article  CAS  Google Scholar 

  85. Mita T, Jacobsen EN (2009) Synlett 1680

    Google Scholar 

  86. Peterson EA, Jacobsen EN (2009) Angew Chem Int Ed 48:6328

    Article  CAS  Google Scholar 

  87. Zuend SJ, Coughlin MP, Lalonde MP, Jacobsen EN (2009) Nature 461:968

    Article  CAS  Google Scholar 

  88. Brown AR, Kuo W-H, Jacobsen EN (2010) J Am Chem Soc 132:9286

    Article  CAS  Google Scholar 

  89. Zuend SJ, Jacobsen EN (2007) J Am Chem Soc 129:15872

    Article  CAS  Google Scholar 

  90. Zuend SJ, Jacobsen EN (2009) J Am Chem Soc 131:15358

    Article  CAS  Google Scholar 

  91. Lu S-F, Du D-M, Zhang S-W, Xu J (2004) Tetrahedron Asymmetr 15:3433

    Article  CAS  Google Scholar 

  92. Du D-M, Lu S-F, Fang T, Xu J (2005) J Org Chem 70:3712

    Article  CAS  Google Scholar 

  93. Lu S-F, Du D-M, Xu J, Zhang S-W (2006) J Am Chem Soc 128:7418

    Article  CAS  Google Scholar 

  94. Lu S-F, Du D-M, Xu J (2006) Org Lett 8:2115

    Article  CAS  Google Scholar 

  95. Liu H, Xu J, Du D-M (2007) Org Lett 9:4725

    Article  CAS  Google Scholar 

  96. Liu H, Lu S-F, Xu J, Du D-M (2008) Chem Asian J 3:1111

    Article  CAS  Google Scholar 

  97. Liu H, Li W, Du D-M (2009) Sci China B 52:1321

    Article  CAS  Google Scholar 

  98. Liu H, Du D-M (2010) Eur J Org Chem 2121

    Google Scholar 

  99. Mihara H, Xu Y, Shepherd NE, Matsunaga S, Shibasaki M (2009) J Am Chem Soc 131:8384

    Article  CAS  Google Scholar 

  100. Shibasaki M, Kanai M, Matsunaga S, Kumagai N (2011) Multimetallic multifunctional catalysts for asymmetric reactions. Top Organomet Chem. doi:10.1007/3418_2011_1

    Google Scholar 

  101. Davies HML, Beckwith REJ (2003) Chem Rev 103:2861

    Article  CAS  Google Scholar 

  102. Nakamura E, Yoshikai N, Yamanaka M (2002) J Am Chem Soc 124:7181

    Article  CAS  Google Scholar 

  103. Covell DJ, White MC (2008) Angew Chem Int Ed 47:6448

    Article  CAS  Google Scholar 

  104. Qi X, Rice GT, Lall MS, Plummer MS, White MC (2010) Tetrahedron 66:4816

    Article  CAS  Google Scholar 

  105. Nakao Y, Yada A, Ebata S, Hiyama T (2007) J Am Chem Soc 129:2428

    Article  CAS  Google Scholar 

  106. Watson MP, Jacobsen EN (2008) J Am Chem Soc 130:12594

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by NIH (5R01GM068433-06), NSF (CHE-0717618), and a Eugene Olshansky Memorial Scholarship (to P.L.).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Hisashi Yamamoto .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2011 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Li, P., Yamamoto, H. (2011). Bifunctional Acid Catalysts for Organic Synthesis. In: Ikariya, T., Shibasaki, M. (eds) Bifunctional Molecular Catalysis. Topics in Organometallic Chemistry, vol 37. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3418_2011_4

Download citation

Publish with us

Policies and ethics