Asymmetric synthesis of (S)-carbinoxamine. New aspects of oxazaborolidine-catalyzed enantioselective carbonyl reduction

Tetrahedron Letters

Volumn 37, Issue 32, 1996, Pages 5675-5678

  Corey, E J ^a   Helal, Christopher J ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBINOXAMINE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS;

EID: 0030570857     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01198-7     Document Type: Article

References (41)

1. 1. Physicians Desk Reference, 44th ed.; Barnhart, E.R.; Medical Economics Co.: N.J., 1990, p. 1898.
2. 2. (a) Roszkowski, A. P.; Govier, W. M. Pharmacologist, 1959,1, 60.
3. (b) Barouh, V.; Dall, H.; Patel, D.; Hite, G. J. Med. Chem. 1971, 14, 834.
4. 3. Braker, W. Br. Pat. 905 993, Sept. 19, 1962. Chem. Abstr. 1963, 58, 5644a.
5. 4. (a) Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551.
6. (b) Corey, E. J.; Bakshi, R. K.; Shibata, S.; Chen, C. P.; Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925.
7. (c) Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Org. Chem. 1988, 53, 2861.
8. (d) Corey, E. J. in Proceedings 31st National Organic Chemistry Symposium of the American Chemical Society; 1989; p 1.
9. (e) Corey, E. J.; Bakshi, R. K. Tetrahedron Lett. 1990, 31, 611.
10. (f) Corey, E. J. Pure Appl. Chem. 1990, 62, 1209.
11. (g) Corey, E. J.; Azimioara, M.; Sarshar, S. Tetrahedron Lett. 1992, 33, 3429.
12. 5. For other applications see: (a) Corey, E. J.; Chen, C. P.; Parry, M. J. Tetrahedron Lett. 1988, 29, 2899 (PAF antagonists).
13. (b) Corey, E. J.; Gavai, A. V. Tetrahedron Lett. 1988, 29, 3201 (ginkgolides A and B).
14. (c) Corey, E. J.; Su, W.-g. Tetrahedron Lett. 1988, 29, 3423; Corey, E. J. Chem. Soc. Rev. 1988, 17, 111 (bilobalide).
15. (c) Corey, E. J.; Su, W.-g. Tetrahedron Lett. 1988, 29, 3423; Corey, E. J. Chem. Soc. Rev. 1988, 17, 111 (bilobalide).
16. (d) Corey, E. J.; Da Silva Jardine, P. Tetrahedron Lett. 1989, 30, 7297 (forskolin).
17. (e) Corey, E. J.; Reichard, G. A. Tetrahedron Lett. 1989, 30, 5207 (fluoxetine).
18. (f) Corey, E. J.; Link, J. O. Tetrahedron Lett. 1989, 30, 6275 (α-deutero alcohols).
19. (g) Corey, E. J.; Link, J. O. Tetrahedron Lett. 1990, 31, 601 (isoproteranol).
20. (h) Corey, E. J.; Link, J. O. J. Org. Chem. 1991, 56, 442 (denopamine).
21. (i) Corey, E. J.; Chen, C. P.; Reichard, G. A. Tetrahedron Lett. 1989, 30, 5547 (chiral oxazaborolidines).
22. (j) Corey, E. J.; Link, J. O. J. Am. Chem. Soc. 1992, 114, 1906 (α-amino acids).
23. (k) Corey, E. J.; Kigoshi, H. Tetrahedron Lett. 1991, 32, 5025 (antheridic acid).
24. (l) Corey, E. J.; Link, J. O. Tetrahedron Lett. 1992, 33, 3431 (α-hydroxy acids).
25. (m) Corey, E. J.; Yi, K. Y.; Matsuda, S. P. T. Tetrahedron Lett. 1992, 33, 2319 (2,3-oxidosqualene).
26. (o) Corey, E. J.; Helal, C. J. Tetrahedron Lett. 1993, 34, 5227 (terminal epoxides).
27. (p) Corey, E. J.; Cimprich, K. A. Tetrahedron Lett. 1992, 33, 4099 (chiral thiols).
28. (q) Corey, E. J.; Cheng, X.-M.; Cimprich, K. A.; Sarshar, S. Tetrahedron Lett. 1991, 32, 6835.
29. 6. Corey, E. J.; Helal, C. J. Tetrahedron Lett. 1995, 36, 9153.
30. 7. Corey, E. J.; Helal, C. J. Tetrahedron Lett., in press.
31. 8. Hayakawa, Y.; Kato, H.; Uchiyama, M.; Kajino, H.; Noyori, R. J. Org. Chem. 1986, 51, 2400.
32. t: 17.7 min, major; 23.0 min, minor).
33. 10. Bojadziev, S. E.; Tsankov, D. T.; Ivanov, P. M.; Berova, N. D. Bull. Chem. Soc. Jpn. 1987, 60, 2651.
34. t: 21.0 min, major; 17.5 min, minor).
35. 12. Corey, E. J.; Cheng, X.-M.; Cimprich, K. A. Tetrahedron Lett. 1991, 32, 6839.
36. 13. Zuccarello, F.; Millefiori, S.; Trovato, S. Can. J. Chem. 1976, 54, 226.
37. 14. For stoichiometric routes to these substrates see (a) Shieh, W.-C.; Cantrell, W. R. Jr.; Carlson, J. A. Tetrahedron Lett. 1995, 36, 3797.
38. (b) Brown, E.; Leze, A; Touet, J. Tetrahedron: Asymmetry 1992, 3, 841.
39. (c) Seebach, D.; Beck, A. K.; Roggo, S.; Wonnacott, A. Chem. Ber. 1985, 118, 3673.
40. (d) Kaino, M.; Ishihara, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1989, 62, 3736.
41. 15. This research was assisted by a grant and a fellowship (to C.J.H.) from the National Science Foundation.