A First Asymmetric Diamination of Olefins

Abstract

An asymmetric diamination of olefins employing stable imidoosmium(VIII) complexes is described for the first time. The reaction is based on the use of chiral acrylic esters and related substrates with enantiopure menthol and 8-phenyl menthol as chiral auxiliaries and gives rise to osmaimidazolidines with good to excellent diastereomeric ratios (up to 95:5). Removal of the osmium centre and the chiral auxiliary leads to novel enantiopure 1,2,3-trisubstituted compounds.