Asymmetric aziridination of N-tert-butanesulfinyl imines with phenyldiazomethane via sulfur ylides

Abstract

Dedicated to Professor Richard A. Bartsch on the occasion of his 70th birthday AbstractOptically active aziridines were synthesized from the reaction of chiral nonracemic N-tertbutanesulfinyl imines with benzyl-stabilized sulfur ylides, wherein the latter were generated from a rhodium-catalyzed decomposition of phenyldiazomethane (PDM) in the presence of various sulfides. In most cases, the aziridines were formed and isolated in quantitative yield and the 2,3-trans-aziridines were found to predominate over the 2,3-cis-aziridine isomers. The diastereoselectivity between the two trans-aziridines was found to vary significantly, depending upon the solvent and sulfide employed in the reaction.