Stereochemistry in the Michael addition of silylcuprate to. alpha.,. beta.-unsaturated sulfoxide

K Takaki, T Maeda, M Ishikawa

Index: Takaki,K.; Maeda,T.; Ishikawa,M. Journal of Organic Chemistry, 1989 ,  vol. 54, p. 58            

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Citation Number: 32

Abstract

Lithium bis (dimethylphenylsily1) cuprate (2), in contrast to dialkylcuprates, reacted with a#- unsaturated sulfoxides 1 to give Michael products 3 and 4 in good yields. The E and 2 sulfoxides 1 afforded predominantly 3 and 4, respectively. When the reaction was quenched with deuterium oxide, four a-deuteriated sulfoxides 5-8 were obtained. While the ratio of 5 to 6 was 9010 from (E)-1 and 70: 30 from (2)-1, 7 and 8 were formed in equal amounts ...