Acylsilane chemistry. Synthesis of regio-and stereoisomerically defined enol silyl ethers using acylsilanes

HJ Reich, RC Holtan, C Bolm

Index: Reich, Hans J.; Holtan, Ronald C.; Bolm, Carsten Journal of the American Chemical Society, 1990 , vol. 112, # 14 p. 5609 - 5617

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Citation Number: 119

Abstract

Abstract: The preparation of enol silyl ethers using a carbonyl addition-Brook rearrangement- elimination sequence was studied. The key intermediate a-silyl-@-X-alkoxides could be prepared in several different ways, including the addition of organolithium or hydride reagents to aX-acylsilanes (path a, using RM with R= alkyl, aryl, vinyl, alkynyl, silyl, stannyl, phosphinyl, and cyano), the addition of aX-lithium reagents to acylsilanes (path b, X= ...

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