In Situ Assembled Boronate Ester Assisted Chiral Carboxylic Acid Catalyzed Asymmetric Trans-Aziridinations

Abstract

We developed herein a new chiral Brønsted acid catalyst which is composed of two independent organic molecules, a chiral diol, and 2-boronobenzoic acid. In situ formation of a boronate ester was utilized as a key process to generate an active catalyst. This boronate ester assisted chiral carboxylic acid catalyst was successfully applied to the trans-aziridination of N-Boc and N-benzyl imines with N-phenyldiazoacetamide. This is the first catalyst to achieve high enantioselectivities using N-benzyl imines.