Practical Asymmetric Synthesis of Vicinal Diamines through the Catalytic Highly Enantioselective Alkylation of Glycine Amide Derivatives

Abstract

Phase-transfer catalysis (PTC) by a designer chiral quaternary ammonium bromide facilitated the direct, highly enantioselective introduction of a wide variety of substituents including cycloalkyl side chains at the α position of the prochiral glycine amide derivative 1. A general, practical procedure for the asymmetric synthesis of structurally diverse monosubstituted vicinal diamines of type 2 is presented. Dpm=diphenylmethyl.