Carbon-Carbon Bond Formation by Selective Coupling of Alkylthioallylcopper Reagent with Allylic Halides

K Oshima, H Yamamoto, H Nozaki

Index: Oshima,K. et al. Bulletin of the Chemical Society of Japan, 1975 , vol. 48, p. 1567 - 1571

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Citation Number: 32

Abstract

The reaction of 1-alkylthioallylcopper reagents with allylic halides affords the SN 2′ type substitution product in excellent yield. The more synthetically useful reagent, 1, 3-bis (methylthio) allylcopper reagent behaves in the same fashion. Attempts to hydrolyze the vinyl sulfide moiety to an aldehyde unit is successful only in the latter case. Yomogi alcohol is synthesized stereospecifically in the light of these results.