α-Thiosubstituted chiral imines/secondary enamines: their use in the asymmetric Michael reaction

…, D Villeneuve, D Desmaële, J d'Angelo, C Riche

Index: Nour, Mohammed; Tan, Kimny; Cave, Christian; Villeneuve, David; Desmaele, Didier; D'Angelo, Jean; Riche, Claude Tetrahedron Asymmetry, 2000 , vol. 11, # 4 p. 995 - 1002

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Citation Number: 16

Abstract

The asymmetric Michael reaction between 2-thiosubstituted chiral imines/secondary enamines derived from (S)-1-phenylethylamine and electrophilic alkenes (methyl acrylate, MVK) was investigated. 2-Phenylthio derivatives furnished the expected Michael adducts with excellent ee. By contrast, an in situ elimination of p-toluenesulfenic acid took place when using the p-toluenesulfinyl analogs.