Issue 3, 2011
From the journal:

Organic & Biomolecular Chemistry

Catalytic asymmetric Michael addition of α,β-unsaturated aldehydes to Ni(ii) complexes of the Schiff base of glycine†

Xiaoyan Luo,a   Zhichao Jin,a   Pengfei Li,a   Jiabin Gao,a   Weimin Yue,a   Xinmiao Lianga  and  Jinxing Ye*a  

* Corresponding authors

a Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai, China
E-mail: yejx@ecust.edu.cn

Abstract

The conjugate addition of Ni(II) complexes of glycine Schiff base to α,β-unsaturated aldehydes catalyzed by (S)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine afforded adducts in excellent yields with up to 49 : 1 dr and 95% ee. This method enables the construction of two adjacent chiral centers in one step, and offers an alternative route to chiral α-amino acid derivatives.

Graphical abstract: Catalytic asymmetric Michael addition of α,β-unsaturated aldehydes to Ni(ii) complexes of the Schiff base of glycine

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Article information

DOI
https://doi.org/10.1039/C0OB00221F
Article type
Paper
Submitted
07 Jun 2010
Accepted
06 Oct 2010
First published
22 Nov 2010

Org. Biomol. Chem., 2011,9, 793-801

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Catalytic asymmetric Michael addition of α,β-unsaturated aldehydes to Ni(II) complexes of the Schiff base of glycine

X. Luo, Z. Jin, P. Li, J. Gao, W. Yue, X. Liang and J. Ye, Org. Biomol. Chem., 2011, 9, 793 DOI: 10.1039/C0OB00221F

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