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A novel synthesis of α, β-unsaturated γ-hydroxy carbonyl compounds from enones with carbon homologation

✍ Scribed by Tsuyoshi Satoh; Shigeyasu Motohashi; Koji Yamakawa

Publisher: Elsevier Science
Year: 1986
Tongue: French
Weight: 203 KB
Volume: 27
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)84671-7

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✦ Synopsis

The alkylation of enone with 1-chloroalkyl phenyl sulfoxide followed by treatment with thiophenolate afforded s-phenylthio-8,y-unsaturated car-bony1 compound, which was oxidized and then hydrolyzed to give a,8-unsaturated y-hydroxy carbonyl compound in good yield. Highly oxygenated ketones and aldehydes are very useful compounds in synthetic organic chemistry. Especially enones and enals are of most important in the chemistry of carbon-carbon bond formation. They are frequently used as dienophiles in the Diels-Alder reaction 2 or as Michael acceptors 3 etc. Recently, we reported4 a new and versatile procedure for synthesizing a-substituted ketones and aldehydes from lower carbonyl compounds with carbon homologation. 5 In the course of studies on the homologation of carbonyl compounds through u,8-epoxy sulfoxides, a new and efficient procedure for the synthesis of a,B-unsaturated y-hydroxy carbonyl compounds from enones was found.

The procedure is given in Scheme 1.

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