Unprecedented Effects of Additives and Ligand-to-Metal Ratio on the Enantiofacial Selection of Copper-Catalyzed Alkynylation of α-Imino Ester with Arylacetylenes

Authors

  • Zhihui Shao,

    1. Open Laboratory of Chirotechnology, Institute of Molecular Technology for Drug Discovery and Synthesis, and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hong Kong, People's Republic of China, Fax: (+852)-23-649-932
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  • Jun Wang,

    1. Open Laboratory of Chirotechnology, Institute of Molecular Technology for Drug Discovery and Synthesis, and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hong Kong, People's Republic of China, Fax: (+852)-23-649-932
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  • Kai Ding,

    1. Open Laboratory of Chirotechnology, Institute of Molecular Technology for Drug Discovery and Synthesis, and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hong Kong, People's Republic of China, Fax: (+852)-23-649-932
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  • Albert S. C. Chan

    1. Open Laboratory of Chirotechnology, Institute of Molecular Technology for Drug Discovery and Synthesis, and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hong Kong, People's Republic of China, Fax: (+852)-23-649-932
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Errata

This article is corrected by:

  1. Errata: Unprecedented Effects of Additives and Ligand-to-Metal Ratio on the Enantiofacial Selection of Copper-Catalyzed Alkynylation of α-Imino Ester with Arylacetylenes Volume 352, Issue 4, 570, Article first published online: 8 March 2010

Abstract

The first catalytic asymmetric addition of arylacetylenes to α-imino esters was carried out using chiral copper(I) complexes as catalysts under mild reaction conditions, providing the corresponding alkynylation products in good yields with 67–74 % ee values. Profound effects of the ligand-to-metal ratio and additives on the stereofacial selection were observed. Both enantiomers of a given product can be obtained with almost identical enantiomeric excess using the same chiral ligand by adjusting the ligand-to-metal ratio.

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