New synthetic methods. 1, 3-Alkylative carbonyl transposition

BM Trost, JL Stanton

Index: Trost,B.M.; Stanton,J.L. Journal of the American Chemical Society, 1975 , vol. 97, p. 4018 - 4025

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Citation Number: 54

Abstract

Abstract: Reaction of carbonyl compounds with vinyllithium reagents followed by quenching with benzenesulfenyl chloride produces the allylic sulfoxide resulting from [2, 3]-sigmatropic rearrangement. Sulfenylation of the corresponding anion results in a net isomerization of the allylic sulfoxide into a y-hydroxy-a, P-unsaturated thioether. Hydrolysis to the enone or enal accomplishes the equivalent of a directed aldol condensation. Application to carbonyl ...