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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
Author(s) -
Reeve Toby B.,
Cros JeanPhilippe,
Gennari Cesare,
Piarulli Umberto,
de Vries Johannes G.
Publication year - 2006
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200504116
Subject(s) - enantiomer , cobalt , chemistry , extraction (chemistry) , yield (engineering) , enantiomeric excess , amino acid , resolution (logic) , reactivity (psychology) , selectivity , organic chemistry , medicinal chemistry , combinatorial chemistry , catalysis , enantioselective synthesis , computer science , materials science , biochemistry , medicine , alternative medicine , pathology , artificial intelligence , metallurgy
Liquidating the assets : Coordination of one enantiomer from a racemic mixture of N ‐benzyl α‐amino acids ( N ‐Bn‐AA) to the lipophilic chiral [Co III (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.