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Synfacts 2008(5): 0528-0528  
DOI: 10.1055/s-2008-1072679
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Three-Component Cyclization to Dihydropyridines

Contributor(s): Benjamin List, Frank Lay
J. Jiang, J. Yu, X.-X. Sun, Q.-Q. Rao, L.-Z. Gong*
Hefei National Laboratry for Physical Sciences at the Microscale and University of Science and Technology of China, Hefei, Chengdu Institute of Organic Chemistry and Graduate School of the Chinese Academy of Sciences, Beijing, P. R. of China
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Publication History

Publication Date:
23 April 2008 (online)

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Significance

The authors developed an asymmetric three-component cyclization reaction between a cinnamaldehyde (1), an aromatic primary amine (2), and a 1,3-dicarbonyl compound (3) to provide 4-aryl substituted 1,4-dihydropyridines 4. The reaction is catalyzed by chiral Brønsted acid 5 in moderate to high yields (31-93% yield) with high to excellent enantiomeric excess (er = 83:17 up to 99:1). Furthermore, two examples of application of the dihydropyridines in the synthesis of optically active heterocyclic compounds are shown.