Chiral Brønsted Acid-Catalyzed Enantioselective Three-Component Povarov Reaction

2009395 citationsJournal Articlegreen Open Access

Authors

Hua Liu · Centre National de la Recherche Scientifique

Guillaume Dagousset · Centre National de la Recherche Scientifique

Géraldine Masson · Institut de Chimie des Substances Naturelles

Pascal Retailleau · Institut de Chimie des Substances Naturelles

Jieping Zhu · Institut de Chimie des Substances Naturelles

Abstract

The three-component Povarov reaction of aldehydes (2), anilines (3), and benzyl N-vinylcarbamate 4 in the presence of 0.1 equiv of chiral phosphoric acid 5 afforded cis-2,4-disubstituted tetrahydroquinolines (1) in good yields and excellent enantiomeric excesses. The shortest synthesis of torcetrapib reported to date, which features this key three-component reaction, is documented.

Topics & Keywords

Asymmetric Synthesis and Catalysis Chemical Synthesis and Analysis Synthetic Organic Chemistry Methods

Publication Details

Published in: Journal of the American Chemical Society

Volume 131, Issue 13, pp. 4598-4599

DOI: 10.1021/ja900806q

Field-Weighted Citation Impact: 22.18

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Chiral Brønsted Acid-Catalyzed Enantioselective Three-Component Povarov Reaction

Authors

Abstract

Topics & Keywords

Publication Details