Aldol Reaction of Aluminium Enolate Resulting from 1,4-Addition of R2AlX to α,β-Unsaturated Carbonyl Compound. A 1-Acylethenyl Anion Equivalent

Abstract

Abstract Organoaluminium reagents R2AlX (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 be an efficient reagent for the same type transformation.