1, 3-Asymmetric induction: highly stereoselective synthesis of 2, 4-trans-disubstituted γ-butyrolactones and γ-butyrothiolactones

…, M Mizutani, Y Furukawa, S Kawamura…

Index: Tamaru, Yoshinao; Mizutani, Masato; Furukawa, Yutaka; Kawamura, Shin-ichi; Yoshida, Zen-ichi; et al. Journal of the American Chemical Society, 1984 , vol. 106, # 4 p. 1079 - 1085

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Citation Number: 124

Abstract

Abstract: A novel 1, 3-trans asymmetric induction has been observed for the halolactonization of a-and a,@-substituted*/, &unsaturated amides. The 1, 3-trans selectivity is lost in the threo diastereomers of amides with a,% OH or@-OAc substituent, due to the 1, 2& directing ability of these substituents.