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Synfacts 2007(3): 0321-0321  
DOI: 10.1055/s-2007-968238
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Multicomponent Domino Reaction

Contributor(s): Benjamin List, Sebastian Hoffmann
A. Carlone, S. Cabrera, M. Marigo, K. A. Jørgensen*
Aarhus University, Denmark
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Publication History

Publication Date:
20 February 2007 (online)

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Significance

An amine-catalyzed enantioselective multicomponent domino reaction leading to substituted cyclohexene carbaldehydes 4 is reported. These products are assumed to be formed via an iminium-iminium-enamine catalysis sequence, starting from two equivalents of an α,β-un­saturated aldehyde (1 = 2) and different activated methylene compounds 3. All products are formed in good diastereomeric ratios and excellent enantioselectivities. Notably, also two different α,β-unsaturated aldehydes (1 ≠ 2) are well tolerated.