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

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)- with various (S)-α-amino acids. The reactions proceed with synthetically useful chemical yields and thermodynamically controlled diastereoselectivit...

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Veröffentlicht in:Organic & biomolecular chemistry 2013-07, Vol.11 (27), p.4503-4507
Hauptverfasser: Sorochinsky, Alexander E, Ueki, Hisanori, Aceña, José Luis, Ellis, Trevor K, Moriwaki, Hiroki, Sato, Tatsunori, Soloshonok, Vadim A
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container_end_page 4507
container_issue 27
container_start_page 4503
container_title Organic & biomolecular chemistry
container_volume 11
creator Sorochinsky, Alexander E
Ueki, Hisanori
Aceña, José Luis
Ellis, Trevor K
Moriwaki, Hiroki
Sato, Tatsunori
Soloshonok, Vadim A
description 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)- with various (S)-α-amino acids. The reactions proceed with synthetically useful chemical yields and thermodynamically controlled diastereoselectivity. Chiral reagent (S)- can be conveniently recovered and reused without any loss of enantiomeric purity and reactivity.
doi_str_mv 10.1039/c3ob40541a
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source MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects Amino Acids - chemical synthesis
Amino Acids - chemistry
Indicators and Reagents
Phenethylamines - chemistry
Stereoisomerism
title Chemical approach for interconversion of (S)- and (R)-α-amino acids
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