Catalytic enantioselective retro-aldol reactions: Kinetic resolution of β-hydroxyketones with aldolase antibodies

Angewandte Chemie - International Edition

Volumn 37, Issue 18, 1998, Pages 2481-2484

  Zhong, Guofu ^a   Shabat, Doron ^a   List, Benjamin ^a   Anderson, James ^a   Sinha, Subhash C ^a   Lerner, Richard A ^a   Barbas III, Carlos F ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Aldol reactions; Asymmetric synthesis; Catalytic antibodies; Enantiomeric resolution; Retro aldol reactions

Indexed keywords

EID: 0032476093     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19981002)37:18<2481::AID-ANIE2481>3.0.CO;2-T     Document Type: Article

References (36)

1. Reviews of the aldol reaction: S. Masamune, W. Choy, J. S. Peterson, L. R. Sita, Angew. Chem. 1985, 97, 1-31; Angew. Chem. Int. Ed. Engl. 1985, 24, 1-30; C. H. Heathcock, Aldrichim. Acta 1990, 23, 99-111; D. A. Evans, Science 1988, 240, 420-426; C. H. Heathcock in Comprehensive Organic Synthesis, Vol. 2 (Eds.: B. M. Trost, I. Flemming, C. H. Heathcock), Pergamon, Oxford, 1991, pp. 133-319; I. Peterson, Pure Appl. Chem. 1992, 64, 1821-1830.
2. Reviews of the aldol reaction: S. Masamune, W. Choy, J. S. Peterson, L. R. Sita, Angew. Chem. 1985, 97, 1-31; Angew. Chem. Int. Ed. Engl. 1985, 24, 1-30; C. H. Heathcock, Aldrichim. Acta 1990, 23, 99-111; D. A. Evans, Science 1988, 240, 420-426; C. H. Heathcock in Comprehensive Organic Synthesis, Vol. 2 (Eds.: B. M. Trost, I. Flemming, C. H. Heathcock), Pergamon, Oxford, 1991, pp. 133-319; I. Peterson, Pure Appl. Chem. 1992, 64, 1821-1830.
3. Reviews of the aldol reaction: S. Masamune, W. Choy, J. S. Peterson, L. R. Sita, Angew. Chem. 1985, 97, 1-31; Angew. Chem. Int. Ed. Engl. 1985, 24, 1-30; C. H. Heathcock, Aldrichim. Acta 1990, 23, 99-111; D. A. Evans, Science 1988, 240, 420-426; C. H. Heathcock in Comprehensive Organic Synthesis, Vol. 2 (Eds.: B. M. Trost, I. Flemming, C. H. Heathcock), Pergamon, Oxford, 1991, pp. 133-319; I. Peterson, Pure Appl. Chem. 1992, 64, 1821-1830.
4. Reviews of the aldol reaction: S. Masamune, W. Choy, J. S. Peterson, L. R. Sita, Angew. Chem. 1985, 97, 1-31; Angew. Chem. Int. Ed. Engl. 1985, 24, 1-30; C. H. Heathcock, Aldrichim. Acta 1990, 23, 99-111; D. A. Evans, Science 1988, 240, 420-426; C. H. Heathcock in Comprehensive Organic Synthesis, Vol. 2 (Eds.: B. M. Trost, I. Flemming, C. H. Heathcock), Pergamon, Oxford, 1991, pp. 133-319; I. Peterson, Pure Appl. Chem. 1992, 64, 1821-1830.
5. Reviews of the aldol reaction: S. Masamune, W. Choy, J. S. Peterson, L. R. Sita, Angew. Chem. 1985, 97, 1-31; Angew. Chem. Int. Ed. Engl. 1985, 24, 1-30; C. H. Heathcock, Aldrichim. Acta 1990, 23, 99-111; D. A. Evans, Science 1988, 240, 420-426; C. H. Heathcock in Comprehensive Organic Synthesis, Vol. 2 (Eds.: B. M. Trost, I. Flemming, C. H. Heathcock), Pergamon, Oxford, 1991, pp. 133-319; I. Peterson, Pure Appl. Chem. 1992, 64, 1821-1830.
6. Reviews of the aldol reaction: S. Masamune, W. Choy, J. S. Peterson, L. R. Sita, Angew. Chem. 1985, 97, 1-31; Angew. Chem. Int. Ed. Engl. 1985, 24, 1-30; C. H. Heathcock, Aldrichim. Acta 1990, 23, 99-111; D. A. Evans, Science 1988, 240, 420-426; C. H. Heathcock in Comprehensive Organic Synthesis, Vol. 2 (Eds.: B. M. Trost, I. Flemming, C. H. Heathcock), Pergamon, Oxford, 1991, pp. 133-319; I. Peterson, Pure Appl. Chem. 1992, 64, 1821-1830.
7. A Yanagisawa, Y. Matsumoto, H. Nakashima, K. Asakawa, H. Yamamoto, J. Am. Chem. Soc. 1997, 119, 9319-9320, and references therein; E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649-3650; D. A. Evans, D. W. C. MacMillan, K. R. Campos, J. Am. Chem. Soc. 1997, 119, 10859-10860; for the only case where ketones and not pre-formed enolates are used see: Y. M. A. Yamada, N. Yoshikawa, H. Sasai, M. Shibasaki, Angew. Chem. 1997, 109, 1942-1944; Angew. Chem. Int. Ed. Engl. 1997, 36, 1871-1873.
8. A Yanagisawa, Y. Matsumoto, H. Nakashima, K. Asakawa, H. Yamamoto, J. Am. Chem. Soc. 1997, 119, 9319-9320, and references therein; E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649-3650; D. A. Evans, D. W. C. MacMillan, K. R. Campos, J. Am. Chem. Soc. 1997, 119, 10859-10860; for the only case where ketones and not pre-formed enolates are used see: Y. M. A. Yamada, N. Yoshikawa, H. Sasai, M. Shibasaki, Angew. Chem. 1997, 109, 1942-1944; Angew. Chem. Int. Ed. Engl. 1997, 36, 1871-1873.
9. A Yanagisawa, Y. Matsumoto, H. Nakashima, K. Asakawa, H. Yamamoto, J. Am. Chem. Soc. 1997, 119, 9319-9320, and references therein; E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649-3650; D. A. Evans, D. W. C. MacMillan, K. R. Campos, J. Am. Chem. Soc. 1997, 119, 10859-10860; for the only case where ketones and not pre-formed enolates are used see: Y. M. A. Yamada, N. Yoshikawa, H. Sasai, M. Shibasaki, Angew. Chem. 1997, 109, 1942-1944; Angew. Chem. Int. Ed. Engl. 1997, 36, 1871-1873.
10. A Yanagisawa, Y. Matsumoto, H. Nakashima, K. Asakawa, H. Yamamoto, J. Am. Chem. Soc. 1997, 119, 9319-9320, and references therein; E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649-3650; D. A. Evans, D. W. C. MacMillan, K. R. Campos, J. Am. Chem. Soc. 1997, 119, 10859-10860; for the only case where ketones and not pre-formed enolates are used see: Y. M. A. Yamada, N. Yoshikawa, H. Sasai, M. Shibasaki, Angew. Chem. 1997, 109, 1942-1944; Angew. Chem. Int. Ed. Engl. 1997, 36, 1871-1873.
11. A Yanagisawa, Y. Matsumoto, H. Nakashima, K. Asakawa, H. Yamamoto, J. Am. Chem. Soc. 1997, 119, 9319-9320, and references therein; E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649-3650; D. A. Evans, D. W. C. MacMillan, K. R. Campos, J. Am. Chem. Soc. 1997, 119, 10859-10860; for the only case where ketones and not pre-formed enolates are used see: Y. M. A. Yamada, N. Yoshikawa, H. Sasai, M. Shibasaki, Angew. Chem. 1997, 109, 1942-1944; Angew. Chem. Int. Ed. Engl. 1997, 36, 1871-1873.
12. a) D. J. Ager, M. B. East, Asymmetric Synthetic Methodology, CRC Press, FL, USA, 1996;
13. b) C.-H. Wong, G. M. Whitesides, Enzymes in Synthetic Organic Chemistry, Pergamon, Oxford, 1994.
14. K. Faber, Biotransformations in Organic Chemistry, 2nd ed., Springer, Berlin, 1995.
15. For an antibody-catalyzed Henry type retro-aldol reaction see: M. E. Flanagan, J. R. Jacobsen, E. Sweet, P. G. Schultz, J. Am. Chem. Soc. 1996, 118, 6078-6079; for a retro-aldol reaction catalyzed by an antibody with an amine cofactor see: J.-L. Reymond, Angew. Chem. 1995, 107, 2471-2473; Angew. Chem. Int. Ed. Engl. 1995, 34, 2285-2287.
16. For an antibody-catalyzed Henry type retro-aldol reaction see: M. E. Flanagan, J. R. Jacobsen, E. Sweet, P. G. Schultz, J. Am. Chem. Soc. 1996, 118, 6078-6079; for a retro-aldol reaction catalyzed by an antibody with an amine cofactor see: J.-L. Reymond, Angew. Chem. 1995, 107, 2471-2473; Angew. Chem. Int. Ed. Engl. 1995, 34, 2285-2287.
17. For an antibody-catalyzed Henry type retro-aldol reaction see: M. E. Flanagan, J. R. Jacobsen, E. Sweet, P. G. Schultz, J. Am. Chem. Soc. 1996, 118, 6078-6079; for a retro-aldol reaction catalyzed by an antibody with an amine cofactor see: J.-L. Reymond, Angew. Chem. 1995, 107, 2471-2473; Angew. Chem. Int. Ed. Engl. 1995, 34, 2285-2287.
18. H. J. M. Gijsen, L. Qiao, W. Fitz, C.-H. Wong, Chem. Rev. 1996, 96, 443-473; C.-H. Wong, R. L. Halcomb, Y. Ichikawa, T. Kajimoto, Angew. Chem. 1995, 107, 453-474; Angew. Chem. Int. Ed. Engl. 1995, 34, 412-432.
19. H. J. M. Gijsen, L. Qiao, W. Fitz, C.-H. Wong, Chem. Rev. 1996, 96, 443-473; C.-H. Wong, R. L. Halcomb, Y. Ichikawa, T. Kajimoto, Angew. Chem. 1995, 107, 453-474; Angew. Chem. Int. Ed. Engl. 1995, 34, 412-432.
20. H. J. M. Gijsen, L. Qiao, W. Fitz, C.-H. Wong, Chem. Rev. 1996, 96, 443-473; C.-H. Wong, R. L. Halcomb, Y. Ichikawa, T. Kajimoto, Angew. Chem. 1995, 107, 453-474; Angew. Chem. Int. Ed. Engl. 1995, 34, 412-432.
21. a) J. Wagner, R. A. Lerner, C. F. Barbas III, Science 1995, 270, 1797-1880;
22. b) R. Björnestedt, G. Zhong, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 1996, 118, 11 720-11 724;
23. c) G. Zhong, T. Hoffmann, R. A. Lerner, S. Danishefsky, C. F. Barbas III, J. Am. Chem. Soc. 1997, 119, 8131-8132;
24. d) C. F. Barbas III, A. Heine, G. Zhong, T. Hoffmann, S. Gramatikova, R. Bjornestedt, B. List, J. Anderson, E. A. Stura, E. A. Wilson, R. A. Lerner, Science 1997, 278, 2085-2092;
25. e) T. Hoffmann, G. Zhong, B. List, D. Shabat, J. Anderson, S. Gramatikova, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 1998, 120, 2768-2779.
26. A. R. Radzicka, R. A. Wolfenden, Science 1995, 267, 90-93.
27. a) N. R. Thomas, Nat. Prod. Rep. 1996, 479-511;
28. b) J. D. Stewart, S. J. Benkovic, Nature 1995, 375, 388-391;
29. c) C-H. L. Lo, P. Wentworth, Jr., K. W. Jung, J. Yoon, J. A. Ashley, K. D. Janda, J. Am. Chem. Soc. 1997, 119, 10 251-10 252.
30. G. Balavoine, A. Moradpour, H. B. Kagan, J. Am. Chem. Soc. 1974, 96, 5152-5158.
31. a) K. D. Janda, S. J. Benkovic, R. A. Lerner, Science 1989, 244, 437-440;
32. b) F. Tanaka, K. Kinoshita, R. Tanimura, I. Fujii, J. Am. Chem. Soc. 1996, 118, 2332-2339;
33. c) H. Wade, T. S. Scanlan, J. Am. Chem. Soc. 1996, 118, 6510-6511;
34. d) S. J. Pollack, P. Hsiun, P. G. Schultz, J. Am. Chem. Soc. 1989, 111, 5961-5962.
35. B. List, D. Shabat, C. F. Barbas III, R. A. Lerner, Chem. Eur. J. 1998, 4, 881-885.
36. I. Paterson, J. A. Channon, Tetrahedron Lett. 1992, 33, 797-800.