Highly stereoselective synthesis of trisubstituted olefins via addition of alkylcopper complexes to acetylenes

A Marfat, PR McGuirk, P Helquist

Index: Marfat,A. et al. Journal of Organic Chemistry, 1979 , vol. 44, # 22 p. 3888 - 3901

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Citation Number: 116

Abstract

Alkylcopper reagents prepared from the reaction of Grignard reagents with the dimethyl sulfide complex of cuprous bromide undergo efficient addition to terminal acetylenes to generate 2, 2-disubstituted alkenylcopper intermediates. The addition also occurs very efficiently with a methylcopper complex despite earlier reports in the literature of difficulty in effecting this reaction. Among the electrophilic species with which the alkenylcopper ...