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Synthesis 2008(18): 2868-2870  
DOI: 10.1055/s-2008-1067234
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Copper(I)-Catalyzed Three-Component Coupling Leading to an Efficient ­Synthesis of β,γ-Alkynyl α-Amino Acid Derivatives

Zhihui Shaoa,b, Albert S. C. Chan*a
a Open Laboratory of Chirotechnology of the Institute of Molecular Technology for Drug Discovery and Synthesis and Department of Applied­ Biology and Chemical Technology, The Hong Kong Polytechnic University, Hong Kong, P. R. of China
Fax: +852(904)23031590; e-Mail: bcachan@polyu.edu.hk;
b Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, P. R. of China
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Publication History

Received 4 March 2008
Publication Date:
22 August 2008 (online)

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Abstract

The first copper(I)-catalyzed direct three-component coupling of ethyl glyoxylate, p-anisidine, and terminal alkynes has been developed. This protocol provides an efficient method to prepare β,γ-alkynyl α-amino acid derivatives in good yields.

Key words

copper - catalysis - multicomponent reactions - β,γ-alkynyl α-amino acids

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9

The promising enantioselectivity has been achieved in the catalytic asymmetric three-component coupling reaction of ethyl glyoxylate, p-anisidine, and terminal alkynes with chiral ligands: Shao, Z. H.; Fan, B. M.; Li, Y. M.; Kwong, F. K. Chan, A. S. C., work in progress.