Recent Applications of α-Amido Sulfones as in situ Equivalents of Activated Imines for Asymmetric Catalytic Nucleophilic Addition Reactions

Abstract

Catalytic nucleophilic addition to the carbon-nitrogen doublebond of an imino group in an asymmetric fashion provides a directconnective and attractive route to enantioenriched N-protected amineswith structural diversity. In the last decades, significant achievementshave been made in the field of catalytic enantioselective reactionsinvolving the use of α-amido sulfones as in situ equivalentsof activated imines. These, in combination with diverse nucleophiles,are used to prepare optically pure amines or N-protected amides.This review focuses on the recent advances in the synthetic applicationsof α-amido sulfones as reactive precursors of imines inthe asymmetric addition of organometallic reagents, Mannich-,aza-Henry, Strecker, and other asymmetric nucleophilic additionreactions. 1 Introduction 2 Asymmetric Mannich-Type Reactions 2.1 Phase-Transfer-Catalyzed Mannich Reactions 2.2 Bifunctional Organocatalyzed Mannich Reactions 3 Catalytic Enantioselective Addition of Organometallic Reagents- 4 Catalytic Enantioselective Aza-Henry Reactions 5 Asymmetric Strecker Reactions 6 Miscellaneous Reactions 7 Summary and Outlook