Enantioselective Syntheses of Substituted γ??Butyrolactones

EL Eliel, X Bai, M Ohwa

Index: Eliel, Ernest L.; Bai, Xu; Ohwa, Masaki Journal of the Chinese Chemical Society, 2000 , vol. 47, # 1 p. 63 - 70

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Citation Number: 14

Abstract

Abstract The previously described chiral 2-acyloxathianes 5 (Scheme I) are used in two different enantioselective syntheses of γ-butyrolactones. In one synthesis, Grignard addition, cleavage and reduction to carbinols RR'C (OH) CH 2 OH is followed by tosylation, malonate homologation, lactonization, and removal of the carbomethoxy group to give optically active γ-lactones. A modification of this synthesis (Scheme I) leads to optically active α- ...