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Reaction of lithium dialkylcuprates with β-acetoxy α,β-unsaturated carbonyl compounds—a new synthesis of substituted α,β-unsaturated carbonyl compounds.

✍ Scribed by Charles P. Casey; David F. Marten; Roger A. Boggs

Publisher: Elsevier Science
Year: 1973
Tongue: French
Weight: 166 KB
Volume: 14
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)86810-6

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✦ Synopsis

Lithium diorganocuprates are now widely used in conjugate additions to a,a-unsaturated car-bony1 compounds' and in coupling reactions with alkyl halides2, allyli~acetates~, and other compounds possessing good leaving groups. Here we report a new reaction of lithium dialkylcuprates which is formally related to both the conjugate addition and coupling reactions. Lithium dialkylcurpates react with the enol acetates of t+dicarbonyl compounds to give the corresponding substituted a,b-unsaturated carbonyl compounds in moderate to excellent yields.

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