Enantioselective trapping of phosphoramidate ammonium ylides with imino esters for synthesis of 2,3-diaminosuccinic acid derivatives

Abstract

A highly enantioselective trapping of protic phosphoramidate ammonium ylides with α-imino esters is reported. The intriguing Rh2(OAc)4 and chiral Brønsted acid co-catalyzed three-component Mannich-type reaction of a diazo compound, a phosphoramidate, and an α-imino ester provides a rapid and efficient access to 2,3-diaminosuccinic acid derivatives with a high level control of diastereo- and enantioselectivity.