The Journal of Organic Chemistry

Regioselective opening of terminal epoxides with 2-(Trialkylsilyl) allyl organometallic reagents

LE Overman, PA Renhowe

Index: Overman, Larry E.; Renhowe, Paul A. Journal of Organic Chemistry, 1994 , vol. 59, # 15 p. 4138 - 4142

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Citation Number: 38

Abstract

Terminal epoxides react with 2-(trialkylsily1) allyl organometallics (Sn, Si, Li, Cu) with varying degrees of efficiency depending upon the nature of the epoxide. The combination of [2-(trimeth-ylsilyl) allylltributylstannane (4) and EtAlC12 is optimum and provides 1- substituted 44trimethylsilyl)-4-penten-l-ol products in good yield.