Synthesis 2007(16): 2576-2580  
DOI: 10.1055/s-2007-983786
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York

Cinchona Alkaloid Based Thiourea Promoted Enantioselective Conjugate Addition of N-Heterocycles to Enones

Jian Wang, Liansuo Zu, Hao Li, Hexin Xie, Wei Wang*
Department of Chemistry and Chemical Biology, University of New Mexico, Albuquerque, NM 87131, USA
Fax: +1(505)2772609; e-Mail: wwang@unm.edu;
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Publikationsverlauf

Received 4 April 2007
Publikationsdatum:
12. Juli 2007 (online)

Abstract

The first enantioselective conjugate addition reaction of 1H-benzotriazole with a variety of enones has been developed. The process, catalyzed by a cinchona alkaloid thiourea, affords Michael adducts in good yields and with moderate to good enantioselectivities.

3

Triazole moieties are important pharmacophores and can be found in many drugs such as Alprazolam, a major agent for the treatment of anxiety, Fluconazole, an antifungal agent, and nucleoside-based Ribavirin, an antiviral drug. Tetrazoles have often been used as bioequivalent replacements for the carboxylic acid group (CO2H) in pharmacologically active compounds because of their favorable physicochemical properties.

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CCDC 292939 contains the supplementary crystallographic data. These data can be obtained free of charge via www.ccdc.cam.ac.uk.