Enantioselective enolborination [15]

Journal of the American Chemical Society

Volumn 120, Issue 5, 1998, Pages 1098-1099

  Ward, D E ^a   Lu, W L ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

BORANE DERIVATIVE; CYCLOHEXANONE DERIVATIVE;

ENANTIOMER; LETTER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032506950     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja973686c     Document Type: Letter

References (34)

1. Houben-Weyl, StereoselectiVe Synthesis; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996.
2. For Reviews, see: (a) Ward, R. S. Chem. Soc. Rev. 1990, 19, 1-19.
3. (b) Gais, H.-J. In Houben-Weyl, StereoselectiVe Synthesis; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Vol. 1, pp 589-644.
4. Heathcock, C. H.; Pirrung, M. C.; Lampe, L.; Buse, C. T.; Young, S. D. J. Org. Chem. 1981, 46, 2290-2300.
5. Ward, D. E.; Liu, Y.; Rhee, C. K. Can. J. Chem. 1994, 72, 1429-1446.
6. (a) Masamune, S.; Choy, W.; Pedersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-76.
7. (b) Nakayama, K. J. Chem. Educ. 1990, 67, 20-23.
8. (c) Roush, W. R.; Hoong, L. H.; Palmer, M. A. J.; Straub, J. A.; Palkowitz, A. D. J. Org. Chem. 1990, 55, 4117-4126.
9. Dhar, R. K. Aldrichimica Acta 1994, 27, 43-51.
10. (a) Wang, Y.-F.; Chen, C.-S.; Girdaukaus, G.; Sih, C. J. J. Am. Chem. Soc. 1984, 106, 3695-3696.
11. (b) Dokuzokic, Z.; Roberts, N. K.; Sawyer, J. F.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1986, 108, 2034-2039.
12. (c) Schreiber, S. L.; Schreiber, T. S.; Smith, D. B. J. Am. Chem. Soc. 1987, 109, 1525-1529.
13. (a) Ward, D. E.; How, D.; Liu, Y. J. Am. Chem. Soc. 1997, 100, 1884-1894.
14. (b) Ward, D. E.; Liu, Y.; How, D. J. Am. Chem. Soc. 1996, 118, 3025-3026.
15. For a Review, see: (a) Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26. Also see ref 2b.
16. (b) For a comprehensive list of references, see: Aoki, K.; Tomioka, K.; Noguchi, H.; Koga, K. Tetrahedron 1997, 53, 13641-13656.
17. (a) Kim, H. D.; Kawasaki, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1989, 30, 6537-6540.
18. (b) Bambridge, K.; Simpkins, N. S. Tetrahedron Lett. 1992, 33, 8141-8144.
19. (c) Bambridge, K.; Clark, B. P.; Simpkins, N. S. J. Chem. Soc., Perkin Trans. 1 1995, 2535-2541.
20. For a Review, see: Cowden, C. J.; Paterson, I. Org. React. 1997, 51, 1-200.
21. Paterson, I.; McClure, C. K.; Schumann, R. C. Tetrahedron Lett. 1989, 30, 1293-1296.
22. (a) Tichy, M.; Malon, P.; Fric, I.; Blaha, K. Collect. Czech. Chem. Commun. 1977, 42, 3591-3604.
23. (b) Cain, C. M.; Cousins, R. P. C.; Coumbarides, G.; Simpkins, N. S. Tetrahedron 1990, 46, 523-544.
24. (c) Shirai, R.; Tanaka, M.; Koga, K. J. Am. Chem. Soc. 1986, 108, 543-545.
25. (d) Bassi, L.; Joos, B.; Gassmann, P.; Kaiser, H. P.; Leuenberger, H.; Kellerschierlein, W. HelV. Chim. Acta 1983, 66, 92-117.
26. (e) Wong, C. H.; Auer, E.; LaLonde, R. T. J. Org. Chem. 1970, 35, 517-519.
27. (a) Evans, D. A.; Nelson, J. V.; Vogel, E.; Taber, T. R. J. Am. Chem. Soc. 1981, 103, 3099-3111.
28. (b) Ganesan, K.; Brown, H. C. J. Org. Chem. 1993, 58, 7162-7169.
29. Corey, E. J.; Yu, C. M.; Kim, S. S. J. Am. Chem. Soc. 1989, 111, 5495-5496.
30. For an example, see: (a) Lattanzi, A.; Bonadies, F.; Scettri, A. Tetrahedron: Asymmetry 1997, 8, 2141-2151.
31. (b) Lattanzi, A.; Bonadies, F.; Senatore, A.; Soriente, A.; Scettri, A. Tetrahedron: Asymmetry 1997, 8, 2473-2478.
32. The ee was determined by optical rotation: Aoki, K.; Nakajima, M.; Tomioka, K.; Koga, K. Chem. Pharm. Bull. 1993, 41, 994-996.
33. Ramachandran, P. V.; Lu, Z.-H.; Brown, H. C. Tetrahedron Lett. 1997, 38, 761-764.
34. Brown, H. C.; Dhar, R. K.; Ganesan, K.; Singaram, B. J. Org. Chem. 1992, 57, 2716-2721.