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Synthesis 2012; 44(11): 1591-1602
DOI: 10.1055/s-0031-1289756
review
© Georg Thieme Verlag Stuttgart · New York

Recent Advances in the Asymmetric Synthesis of α-(Trifluoromethyl)-Containing α-Amino Acids

José Luis Aceña*
a   Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country, 20018 San Sebastián, Spain, Fax: +34 943015270   eMail: joseluis.acena@ehu.es
,
Alexander E. Sorochinsky
a   Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country, 20018 San Sebastián, Spain, Fax: +34 943015270   eMail: joseluis.acena@ehu.es
b   IKERBASQUE, Basque Foundation for Science, 48011 Bilbao, Spain, eMail: vadym.soloshonok@ehu.es
c   Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, Murmanska Street 1, 02660 Kyiv-94, Ukraine
,
Vadim A. Soloshonok*
a   Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country, 20018 San Sebastián, Spain, Fax: +34 943015270   eMail: joseluis.acena@ehu.es
b   IKERBASQUE, Basque Foundation for Science, 48011 Bilbao, Spain, eMail: vadym.soloshonok@ehu.es
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Publikationsverlauf

Received: 20. Februar 2012

Accepted after revision: 20. März 2012

Publikationsdatum:
27. April 2012 (online)

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Abstract

This review article provides a comprehensive update on the development of new methods for the asymmetric synthesis of α-(trifluoromethyl)-α-amino acids, covering the literature from 2006 to mid-February 2012. Most of the methods discussed are based on asymmetric additions across the carbon–nitrogen double bond of the imines derived from esters of 3,3,3-trifluoropyruvic acid. Medium to high levels of stereocontrol can be achieved using phenylglycinol-derived chiral auxiliaries attached to the nitrogen of the corresponding imines. Among the enantioselective approaches, impressive results were achieved through the application of the Strecker­ reaction using chiral thioureas, as well as chiral Brønsted acids, as organocatalysts.

1 Introduction

2 Stoichiometric Asymmetric Syntheses of α-(Trifluoromethyl)-α-amino Acids

3 Catalytic Asymmetric Syntheses of α-(Trifluoromethyl)-α-amino Acids

4 Miscellaneous

5 Conclusions

Key words

asymmetric synthesis - fluorine - amino acids - catalysis - chiral auxiliaries