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Org Lett. 2013 Jul 19;15(14):3598-601. doi: 10.1021/ol401449b. Epub 2013 Jul 5.

Copper-catalyzed enantioselective intramolecular N-arylation, an efficient method for kinetic resolutions.

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1
Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, No.190 Kaiyuan Avenue, Guangzhou Science Park, Guangzhou 510530, China.

Abstract

For the first time, copper-catalyzed intramolecular N-arylation was successfully applied to the kinetic resolution strategy. Under the catalysis of CuI-BINOL derived ligands, the kinetic resolution of rac-2-amino-3-(2-iodoaryl)propionates and rac-2-amino-4-(2-iodoaryl)butanoates afforded chiral intramolecular coupling products and recovered the starting materials in high enantioselectivity (s factors up to 245).

PMID:
23829519
DOI:
10.1021/ol401449b
[Indexed for MEDLINE]
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