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Synfacts 2008(1): 0090-0090  
DOI: 10.1055/s-2007-991411
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Phosphoric Acid Catalyzed Synthesis of 1,4-Dihydropyridines

Contributor(s): Benjamin List, Frank Lay
J. Moreau, A. Duboc, C. Hubert, J.-P. Hurvois, J.-L. Renaud*
Université de Rennes and Ecole Nationale Supérieure de Chimie de Rennes, France
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Publication History

Publication Date:
18 December 2007 (online)

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Significance

A phosphoric acid catalyzed reaction of β-enaminoketones 1 with α,β-unsaturated aldehydes 2 to the corresponding 1,4-dihydropyr­idines 3 is described. By using phosphoric acid 4 moderate to high yields (31-89%) are obtained. Furthermore, the authors have developed an enantioselective 1,4-dihydropyridine synthesis. By employing chiral phosphoric acid catalysts 5a-c moderate enantio­selectivities (er up to 75:25) are achieved.