The development of asymmetric diamination of alkenes with imido-osmium reagents

Abstract

Defined oxidative transformations of alkenes offer a versatile route to higher-functionalised organic entities. While processes such as dihydroxylation and aminohydroxylation have reached a remarkable level of efficiency with regard to substrate scope and enantioselection, the related process of diamination has received only scant attention. This perspective summarises recent results in the development of asymmetric diamination of alkenes employing bis- and tris(imido)osmium oxidants. Two different asymmetric courses were developed which consist of diastereoselective diamination employing chiral auxiliaries and enantioselective diamination in the presence of a chiral metal catalyst. The diamination products are obtained as monomeric diamine-ligated osmium complexes of unprecedented stability, and all results from these studies represent a completely new chapter in osmium-mediated alkene oxidation.