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Synfacts 2007(2): 0210-0210  
DOI: 10.1055/s-2006-955787
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Proline-Catalyzed Aza-Diels-Alder Reaction with Acyclic Unsaturated Ketones

Contributor(s): Benjamin List, Subhas Chandra Pan
F. Aznar*, A.-B. GarcÍa, M.-P. Cabal
Universidad de Oviedo, Spain
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Publication History

Publication Date:
23 January 2007 (online)

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Significance

Here the authors report an (S)-proline-catalyzed imino Diels-Alder reaction between acyclic α,β-unsaturated ketones and aldimines leading to an efficient synthesis of meso-2,6-di­aryl-4-piperidones. With 20 mol% of the catalyst moderate to good yields (21-77%) and high dia­stereoselectivities (dr = 95:5 to 98:2) are obtained for different acyclic α,β-unsaturated ketones with various aryl aldimines.