The Journal of Organic Chemistry

Dichotomous regiochemistry of aldehyde and ketone in the reaction with dithio-substituted crotyllithium

JM Fang, BC Hong, LF Liao

Index: Fang, Jim-Min; Hong, Bor-Cherng; Liao, Li-Fan Journal of Organic Chemistry, 1987 ,  vol. 52,  # 5  p. 855 - 861

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Citation Number: 37

Abstract

The crotyllithium compound 1 generated from (E)-2-(l-propen-l-yl)-1, 3-dithiane reacted with an aldehyde to give y-products in favor of the anti isomer. This regio-and diastereoselective reaction is applicable to syntheses of trans B, y-disubstituted y-lactones, including natural products of (A)-eldanolide and (&)-trans quercus lactone. The y (l, 2)-adducts obtained from the reaction of 1 and enah underwent alkoxy-Cope rearrangements on treatment with KH. ...