Chiral Brønsted Acid-Catalyzed Enantioselective Three-Component Povarov Reaction

Hua Liu, Guillaume Dagousset, Géraldine Masson*, Pascal Retailleau and Jieping Zhu*

*Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France, Email: massonicsn.cnrs-gif.fr, zhuicsn.cnrs-gif.fr

H. Liu, G. Dagousset, G. Masson, P. Retailleau, J. Zhu, J. Am. Chem. Soc., 2009, 131, 4598-4599.

DOI: 10.1021/ja900806q

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Abstract

A three-component Povarov reaction of aldehydes, anilines, and benzyl N-vinylcarbamate in the presence of 0.1 equiv of a chiral phosphoric acid afforded cis-2,4-disubstituted tetrahydroquinolines in good yields and excellent enantiomeric excesses. This three-component reaction enables a very short synthesis of torcetrapib.

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Torcetrapib (CAS: 262352-17-0)

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Key Words

Povarov Reaction, Diels-Alder Reaction, Tetrahydroquinolines, Organocatalysis

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ID: J48-Y2009-1150