Preparation of chlorosilyl enolates

Scott E. Denmark; Robert A. Stavenger; Stephen B.D. Winter; Ken Tsung Wong; Paul A. Barsanti

doi:10.1021/jo981740h

Preparation of chlorosilyl enolates

Scott E. Denmark, Robert A. Stavenger, Stephen B.D. Winter, Ken Tsung Wong, Paul A. Barsanti

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

A variety of chlorosilyl enolates has been prepared starting from esters, thiol esters, acylsilanes, and ketones. Two general methods are involved, direct enolsilylation with trichlorosilyl triflate and diisopropylethylamine, and a number of methods based on electrophilic substitution of either C- or O-silyl or stannyl carbonyl compounds. The most useful method is a Hg(OAc)₂-catalyzed transsilylation from trimethylsilyl to trichlorosilyl enol ethers, providing a wide range of ketone enolates in good to high yield.

Original language	English (US)
Pages (from-to)	9517-9523
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	63
Issue number	25
DOIs	https://doi.org/10.1021/jo981740h
State	Published - Dec 11 1998

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Organic Chemistry

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10.1021/jo981740h

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title = "Preparation of chlorosilyl enolates",

abstract = "A variety of chlorosilyl enolates has been prepared starting from esters, thiol esters, acylsilanes, and ketones. Two general methods are involved, direct enolsilylation with trichlorosilyl triflate and diisopropylethylamine, and a number of methods based on electrophilic substitution of either C- or O-silyl or stannyl carbonyl compounds. The most useful method is a Hg(OAc)2-catalyzed transsilylation from trimethylsilyl to trichlorosilyl enol ethers, providing a wide range of ketone enolates in good to high yield.",

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AU - Denmark, Scott E.

AU - Stavenger, Robert A.

AU - Winter, Stephen B.D.

AU - Wong, Ken Tsung

AU - Barsanti, Paul A.

PY - 1998/12/11

Y1 - 1998/12/11

N2 - A variety of chlorosilyl enolates has been prepared starting from esters, thiol esters, acylsilanes, and ketones. Two general methods are involved, direct enolsilylation with trichlorosilyl triflate and diisopropylethylamine, and a number of methods based on electrophilic substitution of either C- or O-silyl or stannyl carbonyl compounds. The most useful method is a Hg(OAc)2-catalyzed transsilylation from trimethylsilyl to trichlorosilyl enol ethers, providing a wide range of ketone enolates in good to high yield.

AB - A variety of chlorosilyl enolates has been prepared starting from esters, thiol esters, acylsilanes, and ketones. Two general methods are involved, direct enolsilylation with trichlorosilyl triflate and diisopropylethylamine, and a number of methods based on electrophilic substitution of either C- or O-silyl or stannyl carbonyl compounds. The most useful method is a Hg(OAc)2-catalyzed transsilylation from trimethylsilyl to trichlorosilyl enol ethers, providing a wide range of ketone enolates in good to high yield.

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Preparation of chlorosilyl enolates

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