Diastereoselectivity in the Preparation of 4-Phenylthio-4-butanolide Derivatives by the Use of the Pummerer Rearrangement

Article abstract of DOI:10.1246/bcsj.66.2603

Diastereoselectivity in the preparation of 4-phenylthio-4-butanolide derivatives by the Pummerer rearrangement of 4-phenylsulfinylbutanoic acid derivatives was clarified.The reaction of 3-alkyl-4-phenylsulfinylbutanoic acid with acetic anhydride resulted in the predominant formation of trans-3-alkyl-4-phenylthio-4-butanolide.Lactonization of 2,3-dialkyl-4-phenylsulfinylbutanoic acid gave (2RS,3RS,4SR)-2,3-dialkyl-4-phenylthio-4-butanolide predominantly.