A Practical Approach to the Resolution of Racemic N-Benzyl α-Amino Acids by Liquid-Liquid Extraction with a Lipophilic Chiral Salen-Cobalt(III) Complex

Liquidating the assets: Coordination of one enantiomer from a racemic mixture of N‐benzyl α‐amino acids (N‐Bn‐AA) to the lipophilic chiral [CoIII(salen)(OAc)] complex results in its extraction into the organic phase. The enantiomer can then be released in excellent yield and high enantiomeric excess...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2006-04, Vol.45 (15), p.2449-2453
Main Authors: Reeve, Toby B., Cros, Jean-Philippe, Gennari, Cesare, Piarulli, Umberto, de Vries, Johannes G.
Format: Article
Language:English
Subjects:
amino acids
Amino Acids - chemistry
Benzene - chemistry
chiral resolution
cobalt
Cobalt - chemistry
Ethylenediamines - chemistry
Hydrophobic and Hydrophilic Interactions
Lipids - chemistry
molecular recognition
Molecular Structure
N,O ligands
O ligands
Stereoisomerism
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Summary:Liquidating the assets: Coordination of one enantiomer from a racemic mixture of N‐benzyl α‐amino acids (N‐Bn‐AA) to the lipophilic chiral [CoIII(salen)(OAc)] complex results in its extraction into the organic phase. The enantiomer can then be released in excellent yield and high enantiomeric excess by reductive counterextraction. The cobalt(III) complex can be regenerated and re‐used without loss of reactivity or selectivity.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200504116