Synthesis and reactivity of enantiomerically pure N-acylN-alkyl p-toluenesulfinamides

JL García-Ruano, R Alonso, MM Zarzuelo…

Index: Garcia-Ruano, Jose L.; Alonso, Raquel; Zarzuelo, Maria M.; Noheda, Pedro Tetrahedron: Asymmetry, 1995 , vol. 6, # 5 p. 1133 - 1142

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Citation Number: 17

Abstract

The syntheses of different enantiomerically N-acyl N-alkyl p-toluenesulfinamides 5, by N- sulfinylation of primary amines with (S)-menthyl-p-tolylsulfinate followed by N-acylation of the resulting sulfinamides are reported. Their reactions with some C-nucleophiles take place at the sulfur atom exclusively with complete retention of the enantiomeric purity, revealing their ability as sulfinylating agents. In this sense, their comparison with other reagents ...