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

 

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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.

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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.

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