A facile stereoselective synthesis of (2E)-3-silylallylic alcohols by hydromagnesiation of 1-aryl-2-silylacetylenes

European Journal of Organic Chemistry

Volumn , Issue 6, 2006, Pages 1400-1402

  Cai, Mingzhong ^a   Zhou, Zhou ^a   Jiang, Jianwen ^a  

^a JIANGXI NORMAL UNIVERSITY   (China)

Author keywords

(2E) Allylic alcohols; 1 Aryl 2 silylacetylenes; Grignard reaction; Hydromagnesiation; Stereoselective synthesis; Vinyl compounds

Indexed keywords

EID: 33645081197     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200501002     Document Type: Article

References (33)

1. a) T. K. Jones, S. E. Denmark, Org. Synth. 1990, 7, 524-525;
2. b) D. J. Faulkner, Synthesis 1971, 175-189;
3. c) J. Reucroft, P. J. Sammes, Q. Rev. Chem. Soc. 1971, 25, 135-169;
4. d) R. M. Magid, O. S. Fruchey, W. L. Johnson, T. G. Allen, J. Org. Chem. 1979, 44, 359-363;
5. e) K. Takai, S. Sakamoto, T. Isshiki, Org. Lett. 2003, 5, 653-655;
6. f) S. Okamoto, H. Tsujiyama, T. Yoshino, F. Sato, Tetrahedron Lett. 1991, 32, 5789-5792;
7. g) Y. K. Chen, P. J. Walsh, J. Am. Chem. Soc. 2004, 126, 3702-3703.
8. a) J. G. Duboudin, B. Jousseaume, A. Saux, J. Organomet. Chem. 1979, 168, 1-11;
9. b) M. Zaidlewicz, A. Uzarewicz, R. Sarnowski, Synthesis 1979, 62-63;
10. c) A. Ogawa, Y. Tsuboi, R. Obayashi, K. Yokoyama, I. Ryu, N. Sonoda, J. Org. Chem. 1994, 59, 1600-1601;
11. d) E. Negishi, Y. Zhang, F. E. Cederbaum, M. B. Webb. J. Org. Chem. 1986, 51, 4080-4082;
12. e) K. Takai, Y. Kataoka, K. Utimoto, J. Org. Chem. 1990, 55, 1707-1708;
13. f) A. Kamimura, N. Ono, J. Chem. Soc. Chem. Commun. 1988, 1278-1279;
14. g) M. Yukio, S. Kazuhiko, K. Kenji, Chem. Pharm. Bull. 1985, 33, 2531-2534;
15. h) M. Julia, J. N. Verpeaux, Tetrahedron 1983, 39, 3289-3291.
16. W. Oppolzer, R. N. Radinov, Helv. Chim. Acta 1992, 75, 170-174.
17. K. M. Miller, W. S. Huang, T. F. Jamison, J. Am. Chem. Soc. 2003, 125, 3442-3443.
18. J. Chan, T. F. Jamison, J. Am. Chem. Soc. 2003, 125, 11514-11515.
19. P. Wipf, S. Ribe, J. Org. Chem. 1998, 63, 6454-6455.
20. Y. K. Chen, A. E. Lurain, P. J. Walson, J. Am. Chem. Soc. 2002, 124, 12225-12231.
21. Y. H. Kang, C. J. Lee, K. Kim, J. Org. Chem. 2001, 66, 2149-2153.
22. T. Lee, S. Kim, Tetrahedron: Asymmetry 2003, 14, 1951-1954.
23. M. J. Dabdoub, M. L. Begnini, P. G. Guerrero, A. C. M. Baroni, J. Org. Chem. 2000, 65, 61-67.
24. C. C. Silveira, G. Perin, A. L. Braga, M. J. Dabdoub, R. G. Jacob, Tetrahedron 1999, 55, 7421-7432.
25. X. Huang, A. M. Sun, J. Chem. Res. 1999, 292-293.
26. a) D. A. R. Happer, B. E. Steenson, Synthesis 1980, 806-807;
27. b) F. Caturla, C. Najera, Tetrahedron 1997, 53, 11449-11464.
28. X. Huang, M. Xie, Org. Lett. 2002, 4, 1331-1334.
29. a) F. Sato, H. Ishikawa, M. Sato, Tetrahedron Lett. 1981, 22, 85-88;
30. b) F. Sato, H. Watanabe, Y. Tanaka, T. Yamaji, M. Sato, Tetrahedron Lett. 1983, 24, 1041-1044;
31. c) F. Sato, J. Organomet. Chem. 1985, 285, 53-64;
32. d) F. Sato, H. Urabe, in: H. G. Richey Jr (Ed.), Grignard Reagents - New Developments: Hydromagnesiation of Alkenes and Alkynes, Wiley, Chichester, 2000, p. 65-76.
33. M. Alami, F. Ferri, G. Linstrumelle, Tetrahedron Lett. 1993, 34, 6403-6406.