Preparation of chlorosilyl enolates

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

Research output: Contribution to journalArticlepeer-review


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 languageEnglish (US)
Pages (from-to)9517-9523
Number of pages7
JournalJournal of Organic Chemistry
Issue number25
StatePublished - Dec 11 1998

ASJC Scopus subject areas

  • Organic Chemistry


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