Highly Enantio- and Diastereoselective Mannich Reaction of a Chiral Nickel(II) Glycinate with α-Imino Ester for Asymmetric Synthesis of 3-Aminoaspartate

Jiang Wang, Daizong Lin, Jianmei Shi, Xiao Ding, Lei Zhang, Hualiang Jiang, and Hong Liu

Abstract: A 3-aminoaspartate ester was synthesized by a highly enantio- and disatereoselective Mannich reaction of a chiral nickel(II) complex of a Schiff base of glycine with an N-(p-methoxy-phenly)-protected a-imino ester in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene and dichlormethane at toom temperature. This procedure leads to products with up to 99% diastereomeric excess and excellent yields.

Key words: amino acides, asymmetric synthesis, aminoaspartate