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Preparation of silyl enol ethers from acyloin derivatives using silyllithium reagents

โœ Scribed by Bradley D. Robertson; Aaron M. Hartel

Publisher
Elsevier Science
Year
2008
Tongue
French
Weight
121 KB
Volume
49
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

A new method for the regioselective preparation of silyl enol ethers from acyloin derivatives using silyllithium reagents has been developed. Both dimethylphenyl-and methyldiphenylsilyllithium were found to be effective, the latter providing greater stereocontrol. The reaction is believed to proceed via Brook rearrangement assisted by expulsion of the adjacent leaving group. A number of acyclic acyloin derivatives were reacted to form the corresponding silyl enol ethers in good to excellent yield.

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