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Issue 32, 2014
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Design and synthesis of (S)- and (R)-α-(phenyl)ethylamine-derived NH-type ligands and their application for the chemical resolution of α-amino acids

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Abstract

This work presents the first chemical approach for the resolution of α-amino acids offering the following advantages: (1) The specially designed resolving reagent is derived from α-(phenyl)ethylamine, the most inexpensive chiral auxiliary, which can be recycled and reused, rendering the cost structure of the complete process very attractive; (2) the time-efficient two-step process can be conducted under operationally convenient conditions with virtually quantitative yields; and (3) the process can readily be adapted to large-scale use.

Graphical abstract: Design and synthesis of (S)- and (R)-α-(phenyl)ethylamine-derived NH-type ligands and their application for the chemical resolution of α-amino acids

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Supplementary files

Article information


Submitted
29 Mar 2014
Accepted
19 Jun 2014
First published
24 Jun 2014

Org. Biomol. Chem., 2014,12, 6239-6249
Article type
Paper

Design and synthesis of (S)- and (R)-α-(phenyl)ethylamine-derived NH-type ligands and their application for the chemical resolution of α-amino acids

R. Takeda, A. Kawamura, A. Kawashima, H. Moriwaki, T. Sato, J. L. Aceña and V. A. Soloshonok, Org. Biomol. Chem., 2014, 12, 6239
DOI: 10.1039/C4OB00669K

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