Modified cyclization of enantio-enriched α-homoallyloxyalkyllithiums generated by Sn-Li transmetallation: Effects of additives and structural requirement

Heterocycles

Volumn 52, Issue 3, 2000, Pages 1071-1074

  Komine, Nobuyuki ^a   Tomooka, Katsuhiko ^a   Nakai, Takeshi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

LITHIUM CHLORIDE; TETRAHYDROFURAN DERIVATIVE; ZINC BROMIDE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CYCLIZATION; ISOMERISM; STEREOCHEMISTRY;

EID: 0034162660     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-99-s135     Document Type: Article

References (15)

1. Reviews on carbanion cyclization: a) W. F. Bailey and T. V. Ovaska, In Advances in Detailed Reaction Mechanisms, Vol. 3, 1994, pp. 251-273.
2. b) P. Knochel, In Comprehensive Organic Synthesis, Vol. 4, ed. by B. M. Trost and I. Fleming, Pergamon, New York, 1991, pp. 871-872.
3. a) W. F. Bailey, J. J. Patricia, V. C. DelGobbo, R. M. Jarret, and P. J. Okarma, J. Org. Chem., 1985, 50, 1999.
4. b) W. F. Bailey, A. D. Khanolkar, K. Gavaskar, T. V. Ovaska, K. Rossi, Y. Thiel, and K. B. Wiberg, J. Am. Chem. Soc., 1991, 113, 5720.
5. a) K. Tomooka, N. Komine, T. Sasaki, H. Shimizu, and T. Nakai, Tetrahedron Lett., 1998, 39, 9715.
6. b) M. J. Woltering, R. Fröhlich, and D. Hoppe, Angew. Chem., 1997, 109, 1804-1805;
7. Angew. Chem. Int. Ed. Engl., 1997, 36, 1764.
8. a) C. A. Broka, W. J. Lee, and T. Shen, J. Org. Chem., 1988, 55, 1336.
9. b) C. A. Broka and T. Shen, J. Am. Chem. Soc., 1989, 111, 2981.
10. K. Tomooka, N. Komine, and T. Nakai, Tetrahedron Lett., 1997, 38, 8939.
11. N2 reaction with potassium homoallyl alkoxide following our previously reported procedure: K. Tomooka, T. Igarashi, M. Watanabe, and T. Nakai, Tetrahedron Lett., 1992, 33, 5795, and ref. 5.
12. The stereochemistry of 3a was determined in comparison with authentic samples of (2S, 3R)-and (2S, 3S)-isomers: see ref. 5.
13. C. Meyer, I. Marek, G. Courtemanche, and J. F. Normant, Tetrahedron, 1994, 50, 11665.
14. The 2,3-cis-preference cyclization of 5-hexenylzinc has been reported: see ref. 8.
15. (1,3) repulsion in the transition state (i).