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Synthesis 2010(7): 1205-1208  
DOI: 10.1055/s-0029-1219275
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Jiang Wang, Daizong Lin, Jianmei Shi, Xiao Ding, Lei Zhang, Hualiang Jiang, Hong Liu*
Drug Discovery and Design Centre, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Graduate School, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, P. R. of China
Fax: +86(21)50807088; e-Mail: hliu@mail.shcnc.ac.cn;
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Publication History

Received 2 December 2009
Publication Date:
25 January 2010 (online)

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Abstract

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

Key words

amino acids - asymmetric synthesis - aminoaspartate