Kinetic Resolution Using Diastereoselective Acylating Agents as a Synthetic Approach to Enantiopure Amines
Pp. 151-199 (49)
Galina L. Levit, Dmitry A. Gruzdev and Victor P. Krasnov
The kinetic resolution (KR) of racemates is one of the most important
modern approaches to prepare optically pure substances. This method is based on the
difference in the reaction rates of enantiomers under the action of chiral resolving
agents or catalysts. KR as a result of the acylation reaction (acylative KR) has been
widely used to obtain enantiopure amines that are valuable precursors and structural
fragments of biologically active compounds and pharmaceuticals. The nonenzymatic
acylative KR of racemic amines is usually carried out in the presence of chiral acyltransfer
catalysts or by the action of enantioselective or diastereoselective lowmolecular
weight acylating agents.
This review surveys the research work on KR of racemic amines under the action of
chiral diastereoselective acylating agents. This approach has recently received a very
significant development, which is due to the availability of various reagents of this
kind, as well as the ease of process implementation. Application of derivatives of chiral
acids, including natural amino acids, 2-arylpropionic acids, 2-oxy-carboxylic acids, etc.
as acylating agents in the KR processes makes it possible to obtain amines of various
classes and related compounds with a very high enantiomeric purity, which is often
inaccessible in other nonenzymatic methods. Diastereoisomerically enriched (pure)
amides formed as a result of acylative KR of racemic amines may themselves be of
interest for further synthetic transformations.
Acylation, Acyl Chlorides, Amino Acids, 2-Arylpropionic Acids,
Chiral Amines, Enantiomers, 2-Hydroxy Carboxylic Acids, Kinetic Resolution,
Optical Purity, Resolving Agents, Stereoselectivity.
Postovsky Institute of Organic Synthesis, Russian Academy of Sciences (Ural Branch), Ekaterinburg, Russia.