Asymmetric synthesis of (R)-(–)- and (S)-(+)-muscone by enantioselective conjugate addition of chiral dimethylcuprate to (E)-cyclopentadec-2-en-1 -one

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 6, 1991, Pages 1445-1452

  Tanaka, Kazuhiko ^a   Ushio, Hideki ^a   Kawabata, Yasuyuki ^a   Suzuki, Hitomi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049083559     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/P19910001445     Document Type: Article

References (34)

1. H. Walbaum, J. Prakt. Chem., [2], 1906, 73, 488.
2. L. Ruzicka, Helv. Chim. Acta, 1926, 9, 715.
3. L. Ruzicka and M. Stool, Helv. Chim. Acta, 1934, 17, 1308.
4. K. Ziegler and K. Weber, Liebigs Ann. Chem., 1934, 512, 164. For recent reports on the synthesis of racemic muscone
5. H. Suginome and S. Yamada, Tetrahedron Lett., 1987,28,3963 and references cited therein
6. R. W. Thies and K. P. Daruwala, J. Org. Chem., 1987, 52, 3798.
7. S. Stallberg-Stenhagen, Arkiv Kemi, 1951, 3, 517.
8. Q. Branca and A. Fischli, Helv. Chim. Acta, 1977, 60, 925.
9. K. Utimoto, M. Tanaka, M. Kitai and H. Nozaki, Tetrahedron Lett., 1978, 2301.
10. A. Abad, M. Arno, A. Pardo, J. R. Pedro and E. Seoane, Chem. Ind., 1985, 29.
11. D. Terunuma, M. Motegi, M. Tsuda, T. Sawada, H. Nozawa and H. Nohira, J. Org. Chem., 1987, 52, 1630.
12. Z.-F. Xie, H. Suemune and M. Sakai, J. Chem. Soc., Chem. Commun., 1988, 1638.
13. N. Porter, B. Lacher, V. H.-T. Chang and D. R. Magnin, J. Am. Chem. Soc., 1989, 111, 8309.
14. K. A. Nelson and E. A. Mash, J. Org. Chem., 1986, 51, 2721.
15. B. D. Mookherjee, R. R. Patel and W. O. Ledig, J. Org. Chem., 1971, 36,4124.
16. E. J. Corey, R. Naef and F. J. Hannon, J. Am. Chem. Soc., 1986, 108, 7114.
17. R. K. Dieter and M. Tokles, J. Am. Chem. Soc., 1987, 109, 2040, and references cited therein.
18. B. E. Rossiter and M. Eguchi, Tetrahedron Lett., 1990, 31, 965.
19. S. H. Bertz, G. Dabbagh and G. Sunarajan, J. Org. Chem., 1986, 51, 4953
20. R. A. Kretchmer, J. Org. Chem., 1972, 37, 2744
21. J. F. G. A. Jansen and B. L. Feringa, J. Org. Chem., 1990, 55, 4168
22. T. Imamoto and T. Mukaiyama, Chem. Lett., 1980, 45
23. F. Leyendecker and D. Laucher, Tetrahedron Lett., 1983,24, 3517
24. F. Leyendecker, F. Jesser and B. Ruhland, Tetrahedron Lett., 1981, 22, 3601
25. M. Huche, J. Berlan, G. Pourchelet and P. Cresson, Tetrahedron Lett., 1981, 22, 1329.
26. For a preliminary communication, see: K. Tanaka, H. Ushio and H. Suzuki, J. Chem. Soc., Chem. Commun., 1989, 1700.
27. A. H. Beckett, N. T. Lan and G. R. McDonough, Tetrahedron, 1969, 25, 5689.
28. R. A. Chittenden and G. H. Cooper, J. Chem. Soc. C, 1970, 49.
29. D. A. Evans and A. E. Weber, J. Am. Chem. Soc., 1986, 108, 6757.
30. H. Pauling, Helv. Chim. Acta, 1975, 58, 1781.
31. G. Posner, C. E. Whitten and J. J. Sterling, J. Am. Chem. Soc., 1973, 95, 7788.
32. K. Soai, A. Ookawa, K. Ogawa and T. Kaba, J. Chem. Soc., Chem. Commun., 1987, 467
33. T. Mukaiyama, K. Soai, T. Sato, H. Shimizu and K. Suzuki, J. Am. Chem. Soc., 1979, 101, 1455.
34. W. G. Koflon and L. M. Baclawski, J. Org. Chem., 1976, 41, 1879.