Construction of Robust Ruthenium(salen)(CO) Complexes and Asymmetric Aziridination with Nitrene Precursors in the Form of Azide Compounds That Bear Easily Removable N‐Sulfonyl Groups

Abstract

We synthesized new Ru(salen)(CO) complexes of high durability and achieved aziridination with good to excellent enantioselectivity by using azide compounds that contain an easily removable N-sulfonyl group, such as the 2-(trimethylsilyl)ethanesulfonyl group, as a nitrene precursor. Aziridination of less-reactive alpha,beta-unsaturated esters (and amides) proceeded with excellent enantioselectivities, from which it is inferred that an electrophilic species is the active species of this reaction. The present asymmetric aziridination provides a useful tool for introducing optically active nonprotected amine groups.