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Synfacts 2007(9): 0921-0921  
DOI: 10.1055/s-2007-968911
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Synthesis of Dihydropyridinones

Contributor(s): Victor Snieckus, Wei Gan
C. A. Newman, J. C. Antilla, P. Chen, A. V. Predeus, L. Fielding, W. D. Wulff*
Michigan State University, East Lansing, USA and Organon Laboratories Ltd., Newhouse, UK
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Publikationsdatum:
23. August 2007 (online)

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Significance

An asymmetric synthesis of di­hydropyridin-4(1H)-ones by a heteroatom Diels-Alder reaction under a dual Lewis acid catalyst system is reported. The imines derived from aromatic aldehydes are good substrates for this reaction. The excess amount of B(OPh)3 over (S)-VAPOL, essential for obtaining high yields in this reaction, is rationalized by the need of releasing the (S)-VAPOL from binding to the products.