Issue 27, 2013
From the journal:

Organic & Biomolecular Chemistry

Chemical approach for interconversion of (S)- and (R)-α-amino acids

Alexander E. Sorochinsky,abc   Hisanori Ueki,d   José Luis Aceña,a   Trevor K. Ellis,e   Hiroki Moriwaki,f   Tatsunori Satof  and  Vadim A. Soloshonok*ab  

* Corresponding authors

a Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, 20018 San Sebastián, Spain
E-mail: vadym.soloshonok@ehu.es
Fax: +34 943-015270
Tel: +34 943-015177

b IKERBASQUE, Basque Foundation for Science, 48011 Bilbao, Spain

c Institute of Bioorganic Chemistry & Petrochemistry, National Academy of Sciences of Ukraine, Murmanska 1, Kyiv 02660, Ukraine

d International Center for Materials Nanoarchitectonics (MANA), National Institute for Materials Science (NIMS), 1-1, Namiki, Tsukuba, Ibaraki 305-0044, Japan

e Department of Chemistry and Physics, 100 Campus Dr., Weatherford, OK 73096-3098, USA

f Hamari Chemicals Ltd, 1-4-29 Kunijima, Higashi-Yodogawa-ku, Osaka 533-0024, Japan

Abstract

Here we report a general method for the preparation of unnatural (R)-α-amino acids via complexation of α-(phenyl)ethylamine derived chiral reagent (S)-3 with various (S)-α-amino acids. The reactions proceed with synthetically useful chemical yields and thermodynamically controlled diastereoselectivity. Chiral reagent (S)-3 can be conveniently recovered and reused without any loss of enantiomeric purity and reactivity.

Graphical abstract: Chemical approach for interconversion of (S)- and (R)-α-amino acids

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Article information

DOI
https://doi.org/10.1039/C3OB40541A
Article type
Paper
Submitted
18 Mar 2013
Accepted
12 May 2013
First published
13 May 2013

Org. Biomol. Chem., 2013,11, 4503-4507

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Chemical approach for interconversion of (S)- and (R)-α-amino acids

A. E. Sorochinsky, H. Ueki, J. L. Aceña, T. K. Ellis, H. Moriwaki, T. Sato and V. A. Soloshonok, Org. Biomol. Chem., 2013, 11, 4503 DOI: 10.1039/C3OB40541A

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