. ALPHA.,. BETA.-Epoxy sulfoxides as useful intermediates in organic synthesis. 28. A Novel Synthesis Including Asymmetric Synthesis of. ALPHA.,. BETA.- …

…, S Motohashi, N Tokutake, K Yamakawa

Index: Satoh, Tsuyoshi; Motohashi, Shigeyasu; Tokutake, Norio; Yamakawa, Koji Bulletin of the Chemical Society of Japan, 1992 , vol. 65, # 11 p. 2966 - 2973

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Abstract

Reaction of the carbanion derived from 1-chloroalkyl aryl sulfoxides with enones gave 1, 2- adducts in good yields. Treatment of the adduct with potassium benzenethiolate afforded α- phenylthio β, γ-unsaturated carbonyl compound through an α, β-epoxy sulfoxide. Oxidation of the sulfide with 2.1 equivalents of m-chloroperbenzoic acid gave α, β-unsaturated γ- phenylsulfinyloxy carbonyl compound via sulfoxide-sulfenate rearrangement. The ...