Highly enantioselective zinc/BINOL-catalyzed alkynylation of α-ketoimine ester: a new entry to optically active quaternary α-CF3 α-amino acids

Gaochao Huang; Jie Yang; Xingang Zhang

doi:10.1039/C1CC10403A

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Highly enantioselective zinc/BINOL-catalyzed alkynylation of α-ketoimine ester: a new entry to optically active quaternary α-CF₃ α-amino acids†

Gaochao Huang,‡^a Jie Yang ‡^b and Xingang Zhang*^a

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* Corresponding authors

^a Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 3, 45 Lingling Road, Shanghai 200032, China
E-mail: xgzhang@mail.sioc.ac.cn
Fax: (+86)-21-6416-6128
Tel: (+86)-21-5492-5333

^b Graduate School of Southwest Petroleum University, 8 Xindu Avenue, Chengdu 610065, China

Abstract

An effective method for highly enantioselective alkynylation of ketoimine (α-trifluoromethyl ketoimine ester) has been developed via a zinc/BINOL catalyzed process. This protocol provides a useful and facile access to optically active quaternary α-trifluoromethyl α-amino acids and related derivatives of interest in life sciences.

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Article information

DOI: https://doi.org/10.1039/C1CC10403A
Article type: Communication
Submitted: 20 Jan 2011
Accepted: 10 Mar 2011
First published: 05 Apr 2011

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Chem. Commun., 2011,47, 5587-5589

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Highly enantioselective zinc/BINOL-catalyzed alkynylation of α-ketoimine ester: a new entry to optically active quaternary α-CF₃ α-amino acids

G. Huang, J. Yang and X. Zhang, Chem. Commun., 2011, 47, 5587 DOI: 10.1039/C1CC10403A

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Chemical Communications