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Synfacts 2010(4): 0477-0477  
DOI: 10.1055/s-0029-1219514
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

α-Chlorination of β-Keto Esters Catalyzed by a Bifunctional N-Oxide/Amide Catalyst

Contributor(s): Benjamin List, Ilija Čorić
Y. Cai, W. Wang, K. Shen, J. Wang, X. Hu, L. Lin, X. Liu, X. Feng*
Sichuan University, Chengdu, P. R. of China
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Publication History

Publication Date:
22 March 2010 (online)

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Significance

A new organocatalytic system was developed for the asymmetric α-chlorination of ­cyclic β-keto esters 2 using N-chlorosuccinimide (NCS) as the chlorine source. C 2-Symmetric catalyst 1 possessing N-oxide and amide functionalities provided α-chloro-β-keto esters 3 in high yields with high enantioselectivity. In contrast to the chlorination reaction, bromination and iodination reactions resulted in diminished enantioselectivity.