Enantioselective acylations catalyzed by chiral phosphines

Journal of Organic Chemistry

Volumn 61, Issue 2, 1996, Pages 430-431

  Vedejs, E ^a   Daugulis, O ^a   Diver, S T ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001526323     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951661v     Document Type: Article

References (43)

1. Wegler, R. Liebigs Ann. Chem. 1932, 498, 62. Wegler, R. Liebigs Ann. Chem. 1933, 506, 77. Wegler, R. Liebigs Ann. Chem. 1934, 510, 72. Wegler, R.; Rüber, A. Chem. Ber. 1935, 68, 1055.
2. Wegler, R. Liebigs Ann. Chem. 1932, 498, 62. Wegler, R. Liebigs Ann. Chem. 1933, 506, 77. Wegler, R. Liebigs Ann. Chem. 1934, 510, 72. Wegler, R.; Rüber, A. Chem. Ber. 1935, 68, 1055.
3. Wegler, R. Liebigs Ann. Chem. 1932, 498, 62. Wegler, R. Liebigs Ann. Chem. 1933, 506, 77. Wegler, R. Liebigs Ann. Chem. 1934, 510, 72. Wegler, R.; Rüber, A. Chem. Ber. 1935, 68, 1055.
4. Wegler, R. Liebigs Ann. Chem. 1932, 498, 62. Wegler, R. Liebigs Ann. Chem. 1933, 506, 77. Wegler, R. Liebigs Ann. Chem. 1934, 510, 72. Wegler, R.; Rüber, A. Chem. Ber. 1935, 68, 1055.
5. Reviews: Sih, C. J.; Wu, S.-H. Topics Stereochem. 1989,19, 63. Chen, C.-S.; Sih, C. J. Angew. Chem., Int. Ed., Engl. 1989, 28, 695. Klibanov, A. M. Acc. Chem. Res. 1990, 23, 114. Ward, S. C. Chem. Rev. 1990, 90, 1. Drueckhammer, D. G.; Hennen, W. J.; Pederson, R. L.; Barbas, C. F., III; Gautheron, C. M.; Krach, T.; Wong, C.-H. Synthesis 1991. 499. Haraldsson, G. G. The Application of Lipases in Organic Synthesis. In The Chemistry of Functional Groups, Suppl. B, The Chemistry of Acid Derivatives; Patai, S., Ed.; John Wiley & Sons: Chichester, 1992; Vol. 2, p 1395. Roberts, S. M. Chimia 1993, 47, 85.
6. Reviews: Sih, C. J.; Wu, S.-H. Topics Stereochem. 1989,19, 63. Chen, C.-S.; Sih, C. J. Angew. Chem., Int. Ed., Engl. 1989, 28, 695. Klibanov, A. M. Acc. Chem. Res. 1990, 23, 114. Ward, S. C. Chem. Rev. 1990, 90, 1. Drueckhammer, D. G.; Hennen, W. J.; Pederson, R. L.; Barbas, C. F., III; Gautheron, C. M.; Krach, T.; Wong, C.-H. Synthesis 1991. 499. Haraldsson, G. G. The Application of Lipases in Organic Synthesis. In The Chemistry of Functional Groups, Suppl. B, The Chemistry of Acid Derivatives; Patai, S., Ed.; John Wiley & Sons: Chichester, 1992; Vol. 2, p 1395. Roberts, S. M. Chimia 1993, 47, 85.
7. Reviews: Sih, C. J.; Wu, S.-H. Topics Stereochem. 1989,19, 63. Chen, C.-S.; Sih, C. J. Angew. Chem., Int. Ed., Engl. 1989, 28, 695. Klibanov, A. M. Acc. Chem. Res. 1990, 23, 114. Ward, S. C. Chem. Rev. 1990, 90, 1. Drueckhammer, D. G.; Hennen, W. J.; Pederson, R. L.; Barbas, C. F., III; Gautheron, C. M.; Krach, T.; Wong, C.-H. Synthesis 1991. 499. Haraldsson, G. G. The Application of Lipases in Organic Synthesis. In The Chemistry of Functional Groups, Suppl. B, The Chemistry of Acid Derivatives; Patai, S., Ed.; John Wiley & Sons: Chichester, 1992; Vol. 2, p 1395. Roberts, S. M. Chimia 1993, 47, 85.
8. Reviews: Sih, C. J.; Wu, S.-H. Topics Stereochem. 1989,19, 63. Chen, C.-S.; Sih, C. J. Angew. Chem., Int. Ed., Engl. 1989, 28, 695. Klibanov, A. M. Acc. Chem. Res. 1990, 23, 114. Ward, S. C. Chem. Rev. 1990, 90, 1. Drueckhammer, D. G.; Hennen, W. J.; Pederson, R. L.; Barbas, C. F., III; Gautheron, C. M.; Krach, T.; Wong, C.-H. Synthesis 1991. 499. Haraldsson, G. G. The Application of Lipases in Organic Synthesis. In The Chemistry of Functional Groups, Suppl. B, The Chemistry of Acid Derivatives; Patai, S., Ed.; John Wiley & Sons: Chichester, 1992; Vol. 2, p 1395. Roberts, S. M. Chimia 1993, 47, 85.
9. Reviews: Sih, C. J.; Wu, S.-H. Topics Stereochem. 1989,19, 63. Chen, C.-S.; Sih, C. J. Angew. Chem., Int. Ed., Engl. 1989, 28, 695. Klibanov, A. M. Acc. Chem. Res. 1990, 23, 114. Ward, S. C. Chem. Rev. 1990, 90, 1. Drueckhammer, D. G.; Hennen, W. J.; Pederson, R. L.; Barbas, C. F., III; Gautheron, C. M.; Krach, T.; Wong, C.-H. Synthesis 1991. 499. Haraldsson, G. G. The Application of Lipases in Organic Synthesis. In The Chemistry of Functional Groups, Suppl. B, The Chemistry of Acid Derivatives; Patai, S., Ed.; John Wiley & Sons: Chichester, 1992; Vol. 2, p 1395. Roberts, S. M. Chimia 1993, 47, 85.
10. Reviews: Sih, C. J.; Wu, S.-H. Topics Stereochem. 1989,19, 63. Chen, C.-S.; Sih, C. J. Angew. Chem., Int. Ed., Engl. 1989, 28, 695. Klibanov, A. M. Acc. Chem. Res. 1990, 23, 114. Ward, S. C. Chem. Rev. 1990, 90, 1. Drueckhammer, D. G.; Hennen, W. J.; Pederson, R. L.; Barbas, C. F., III; Gautheron, C. M.; Krach, T.; Wong, C.-H. Synthesis 1991. 499. Haraldsson, G. G. The Application of Lipases in Organic Synthesis. In The Chemistry of Functional Groups, Suppl. B, The Chemistry of Acid Derivatives; Patai, S., Ed.; John Wiley & Sons: Chichester, 1992; Vol. 2, p 1395. Roberts, S. M. Chimia 1993, 47, 85.
11. Reviews: Sih, C. J.; Wu, S.-H. Topics Stereochem. 1989,19, 63. Chen, C.-S.; Sih, C. J. Angew. Chem., Int. Ed., Engl. 1989, 28, 695. Klibanov, A. M. Acc. Chem. Res. 1990, 23, 114. Ward, S. C. Chem. Rev. 1990, 90, 1. Drueckhammer, D. G.; Hennen, W. J.; Pederson, R. L.; Barbas, C. F., III; Gautheron, C. M.; Krach, T.; Wong, C.-H. Synthesis 1991. 499. Haraldsson, G. G. The Application of Lipases in Organic Synthesis. In The Chemistry of Functional Groups, Suppl. B, The Chemistry of Acid Derivatives; Patai, S., Ed.; John Wiley & Sons: Chichester, 1992; Vol. 2, p 1395. Roberts, S. M. Chimia 1993, 47, 85.
12. Evans, D. A.; Anderson, J. C.; Taylor, M. K. Tetrahedron Lett. 1993, 34, 5563.
13. (a) Bird, C. W. Tetrahedron 1962, 18, 1.
14. (b) Weidmann, R.; Horeau, A. Bull. Soc. Chim. Fr. 1967, 117.
15. (c) Stegman, W.; Uebelhart, P.; Heimgartner, H.; Schmid, H. Tetrahedron Lett. 1978, 19, 3091.
16. (d) Mukaiyama, T.; Tomioka, L; Shimizu, M. Chem. Lett. 1984, 49. Ichikawa, J.; Asami, M ; Mukaiyama, T. Chem. Lett. 1984, 949.
17. (d) Mukaiyama, T.; Tomioka, L; Shimizu, M. Chem. Lett. 1984, 49. Ichikawa, J.; Asami, M ; Mukaiyama, T. Chem. Lett. 1984, 949.
18. (d) Duhamel, L.; Herman, T. Tetrahedron Lett. 1985, 26, 3099.
19. 3 (>2%, ee not assayed).
20. (g) Potapov, V. M.; Dem'yanovich, V. M.; Klebnikov, V. A.; Korovina, T. G. Zh. Org. Khim. 1986, 22, 1218 (English transi., 1095)
21. (h) Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett. 1994, 611.
22. Vedejs, E.; Diver, S. T. J. Am. Chem. Soc. 1993, 115, 3358. Vedejs, E.; Bennett, N. S.; Conn, L. M.; Diver, S. T.; Gingras, M.; Lin, S.; Oliver, P. A.; Peterson, M. J. J. Org. Chem. 1993, 58, 7286.
23. Vedejs, E.; Diver, S. T. J. Am. Chem. Soc. 1993, 115, 3358. Vedejs, E.; Bennett, N. S.; Conn, L. M.; Diver, S. T.; Gingras, M.; Lin, S.; Oliver, P. A.; Peterson, M. J. J. Org. Chem. 1993, 58, 7286.
24. Cherkasova, E. M.; Bogatkov, S. V.; Golovina, Z. P. Russ. Chem. Rev. 1977, 46, 246.
25. MacNeil, P. A.; Roberts, N. K.; Bosnich, B. J. Am. Chem. Soc. 1981, 103, 2273.
26. Gladiali, S.; Dore, A.; Fabbri, D.; De Lucchi, O.; Manassero, M. Tetrahedron: Asymmetry 1994, 5, 511.
27. Burk, M. J.; Feaster, J. E.; Harlow, R. L. Tetrahedron: Asymmetry 1991, 2, 569.
28. Laumen, K.; Seemayer, R.; Schneider, M. P. J. Chem. Soc., Chem. Commun. 1990, 49. Gotoh, S.; Aoki, M.; Iwaeda, T.; Izumi, S.; Hirata, T. Chem. Lett. 1994, 1519.
29. Laumen, K.; Seemayer, R.; Schneider, M. P. J. Chem. Soc., Chem. Commun. 1990, 49. Gotoh, S.; Aoki, M.; Iwaeda, T.; Izumi, S.; Hirata, T. Chem. Lett. 1994, 1519.
30. Aoyama, T.; Shiori, T. Tetrahedron Lett. 1990, 31, 5507.
31. Xie, Z.-F.; Suemune, H.; Sakai, K. J. Chem. Soc., Chem. Commun. 1987, 838. Xie, Z.-F.; Nakamura, I.; Suemune, H.; Sakai, K. J. Chem. Soc., Chem. Commun. 1988, 966.
32. Xie, Z.-F.; Suemune, H.; Sakai, K. J. Chem. Soc., Chem. Commun. 1987, 838. Xie, Z.-F.; Nakamura, I.; Suemune, H.; Sakai, K. J. Chem. Soc., Chem. Commun. 1988, 966.
33. (a) Rieche, A.; Schmitz, E.; Schade, W.; Beyer, E. Chem. Ber. 1961, 94, 2926 Lundt, I.; Pedersen, C. Acta Chem. Scand. 1972, 26, 1938.
34. (a) Rieche, A.; Schmitz, E.; Schade, W.; Beyer, E. Chem. Ber. 1961, 94, 2926 Lundt, I.; Pedersen, C. Acta Chem. Scand. 1972, 26, 1938.
35. (b) Glass, B. D.; Goosen, A.; McCleland, C. W. J. Chem. Soc., Perkin Trans. 2 1993, 2175.
36. (a) Anchisi, C., Maccioni, A.; Maccioni, A. M.; Podda, G. Gazz. Chim. Ital. 1983, 113, 73.
37. (b) Davis, F. A.; Haque, S.; Przeslawski, R. M. J. Org. Chem. 1989, 54, 2021.
38. (c) Mango, F. D.; Bonner, W. A. J. Org. Chem. 1964, 29, 1367.
39. Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249.
40. Rule, H. G.; Paterson, T. R. J. Chem. Soc. 1924, 2155.
41. (a) Clark, R. D.; Mosher, H. S. J. Org. Chem. 1970, 35, 1114.
42. (b) Falorni, M.; Lardicci, L.; Rosini, C.; Giacomelli, G. J. Org. Chem. 1986, 51, 2030.
43. The reaction of 1b using perdeuterated acetic anhydride/6a gave monoacetate 7b without loss of deuterium at the acetate methyl group (NMR assay), thus ruling out a ketene mechanism.