Tert-Butanesulfinimines: Structure, synthesis and synthetic applications

Abstract

Since Ellman’s seminal works, over the past ten years tert-butanesulfinimines have proved to be useful chiral amino intermediates for organic synthesis. Through highly stereoselective reactions, amongst which reductions, nucleophilic 1,2-additions and ylide condensations, a broad range of nitrogen-containing compounds has been synthesized. Although the stereoselectivity levels are high in most cases, the sense of the stereoinduction is generally not predictable. The object of this critical review is to present the models proposed to rationalize the stereochemical outcome of the reactions involving tert-butanesulfinimines and to point out an obvious lack of homogeneity amongst them (128 references). © 2009 The Royal Society of Chemistry.