Chemistry Letters

Novel asymmetric alkylation of cyclic. BETA.-keto esters with optically active sulfonium salts.

…, K Umemura, N Watanabe, H Matsuyama

Index: Kobayashi, Michio; Umemura, Kazuyuki; Watanabe, Nobuko; Matsuyama, Haruo Chemistry Letters, 1985 , p. 1067 - 1070

Full Text: HTML

Citation Number: 17

Abstract

A new asymmetric alkylation of cyclic β-keto esters with optically active sulfonium salts, which are easily prepared by optical resolution methods, has been investigated. Relative reactivities for alkyl substituents are found to be quite different from those for SN 2 alkylation. Stereochemical reaction course via S–O sulfurane intermediate for this new reaction is proposed.

Related Articles:

Asymmetric alkylation of. beta.-keto esters with optically active sulfonium salts

[Umemura, Kazuyuki; Matsuyama,Haruo; Watanabe, Nobuko; Kobayashi, Michio; Kamigata, Nobumasa Journal of Organic Chemistry, 1989 , vol. 54, # 10 p. 2374 - 2383]

Rearrangement of suitably constituted aryl, alkyl, or vinyl radicals by acyl or cyano group migration

[Beckwith,A.L.; O'Shea,D.M.; Westwood,S.W. Journal of the American Chemical Society, 1988 , vol. 110, p. 2565]

Rearrangement of suitably constituted aryl, alkyl, or vinyl radicals by acyl or cyano group migration

[Beckwith,A.L.; O'Shea,D.M.; Westwood,S.W. Journal of the American Chemical Society, 1988 , vol. 110, p. 2565]

Rearrangement of suitably constituted aryl, alkyl, or vinyl radicals by acyl or cyano group migration

[Beckwith,A.L.; O'Shea,D.M.; Westwood,S.W. Journal of the American Chemical Society, 1988 , vol. 110, p. 2565]

Cyclizations of unsaturated. bul. CR (COX) 2 radicals. Manganese (III) acetate oxidative cyclizations of unsaturated acetoacetates and atom-transfer cyclizations of …

[Curran, Dennis P.; Morgan, Tina M.; Eric Schwartz; Snider, Barry B.; Dombroski, Mark A. Journal of the American Chemical Society, 1991 , vol. 113, # 17 p. 6607 - 6617]

More Articles...