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Synfacts 2006(12): 1280-1280  
DOI: 10.1055/s-2006-955559
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Brønsted Acid Catalyzed Aza-Diels-Alder Reaction

Contributor(s): Benjamin List, Sebastian Hoffmann
T. Akiyama*, H. Morita, K. Fuchibe
Gakushuin University, Tokyo, Japan
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Publication History

Publication Date:
22 November 2006 (online)

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Significance

A Brønsted acid catalyzed enantio­selective inverse electron-demand aza-Diels-Alder reaction leading to tetrahydroquinoline derivatives 3 is described. In the course of the reaction imine 1 is presumably activated via protonation and further reacts with an electron-rich alkene 2. A chiral phosphoric acid 4, derived from (R)-binol, was employed as catalyst, leading to tetrahydroquinolines 3 with high enantiomeric ratios.