Ynol silyl ethers via O-silylation of ester-derived ynolate anions

CJ Kowalski, GS Lal, MS Haque

Index: Kowalski, Conrad J.; Lal, Sankar G.; Haque, Serajul M. Journal of the American Chemical Society, 1986 , vol. 108, # 22 p. 7127 - 7128

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Citation Number: 46

Abstract

Herein we report that lithium ynolate anions 1, derived from esters 3 using our previously described homologation method, 2 react with chlorotrialkylsilanes on oxygen to afford silyl ynol ethers 2. This represents the first silylation of ynolate anions on~ xygen,~ in contrast to literature reports4 in which reactions with chlorotrimethylsilane resulted in formation of only the corresponding ketenes (4). In our hands, chlorotrimethylsilane treatment of ynolate ...