Copper-mediated substitution reactions of alkylmagnesium reagents with allylic carbamates:(Z)-selective alkene synthesis

JH Smitrovich, KA Woerpel

Index: Smitrovich; Woerpel Journal of the American Chemical Society, 1998 , vol. 120, # 49 p. 12998 - 12999

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Citation Number: 42

Abstract

Copper-mediated allylic substitution reactions represent important methods for the construction of alkenes. 1, 2 Both alkyllithium and alkylmagnesium reagents have been used since the initial report of these reactions with allylic acetates. 3 The regiochemistry of substitution with diorganocuprates is dependent upon the level of substitution of the allylic substrate, with substitution at the least hindered terminus predominating. Protocols have ...