Aldol Reaction of Aluminium Enolate Resulting from 1, 4-Addition of R 2 AlX to α, β-Unsaturated Carbonyl Compound. A 1-Acylethenyl Anion Equivalent

A Itoh, S Ozawa, K Oshima, H Nozaki

Index: Itoh, Akira; Ozawa, Shuji; Oshima, Koichiro; Nozaki, Hitosi Bulletin of the Chemical Society of Japan, 1981 , vol. 54, # 1 p. 274 - 278

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Citation Number: 87

Abstract

Organoaluminium reagents R 2 AlX (X= SPh, SeMe) easily add to α, β-unsaturated carbonyl compounds in 1, 4-fashion. The resulting aluminium enolates react with aldehydes to give aldol adducts in fair to good yields. Formal elimination of HX from the adducts provides α- substituted α, β-unsaturated carbonyl compounds. The overall transformation is an addition of aldehydes to 1-acylethenyl anion equivalent. Diethylaluminium iodide also is found to ...