Issue 42, 2010
From the journal:

Chemical Communications

Highly diastereoselective synthesis of quaternary α-trifluoromethyl α-amino acids from chiral imines of trifluoropyruvate†‡

Qiao-Qiao Min,b   Chun-Yang He,a   Haibing Zhoub  and  Xingang Zhang*a  

* Corresponding authors

a Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China
E-mail: xgzhang@mail.sioc.ac.cn
Fax: (+86)-21-6416-6128
Tel: (+86)-21-5492-5333

b State Key Laboratory of Virology, College of Pharmacy, Wuhan University, Wuhan, China

Abstract

An efficient method for highly diastereoselective synthesis of quaternary α-trifluoromethyl α-amino acids was developed via indium mediated allylation of (R)-phenylglycinol methyl ether based imines of trifluoropyruvate in good yields with high diastereoselectivities at room temperature; to illustrate the application of this method in organic synthesis, 2-allyl-2-(trifluoromethyl) aziridine was prepared in an efficient manner.

Graphical abstract: Highly diastereoselective synthesis of quaternary α-trifluoromethyl α-amino acids from chiral imines of trifluoropyruvate

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Article information

DOI
https://doi.org/10.1039/C0CC02408B
Article type
Communication
Submitted
07 Jul 2010
Accepted
01 Sep 2010
First published
20 Sep 2010

Chem. Commun., 2010,46, 8029-8031

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Highly diastereoselective synthesis of quaternary α-trifluoromethyl α-amino acids from chiral imines of trifluoropyruvate

Q. Min, C. He, H. Zhou and X. Zhang, Chem. Commun., 2010, 46, 8029 DOI: 10.1039/C0CC02408B

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