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Synthesis 2009(10): 1744-1752  
DOI: 10.1055/s-0028-1088075
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart ˙ New York

Highly Diastereoselective Conjugate Addition-Elimination of Chiral Nickel(II) Glycinate with Activated Allylic Acetates for Asymmetric Synthesis of Glutamic Acid Derivatives

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

Received 13 March 2009
Publication Date:
27 April 2009 (online)

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Abstract

A practically feasible, diastereoselective conjugate addition-elimination reaction of a chiral nickel(II) complex of glycine 1 with allylic acetates 2 is described. The reaction pathway was successfully controlled, and the desired formation of a carbon-carbon bond was exclusively obtained with high diastereoselectivity. This reaction is an attractive route for the asymmetric synthesis of previously unavailable chainlike glutamic acid derivatives.

Key words

nickel(II) complex - asymmetric synthesis - glutamic acid - amino acids

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