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Synfacts 2009(11): 1283-1283  
DOI: 10.1055/s-0029-1218112
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Aminocatalysis Cascades of Enones

Contributor(s): Benjamin List, Steffen Müller
L.-Y. Wu, G. Bencivenni, M. Mancinelli, A. Mazzanti, G. Bartoli, P. Melchiorre*
Università di Bologna, Italy
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Publication History

Publication Date:
22 October 2009 (online)

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Significance

The authors identified the cinchona alkaloid derived primary amine 1 in combination with acid 2 as a powerful catalyst system for organocatalytic cascade reactions of enones. Employing nitroalkenes as reaction partners, the corresponding cyclohexanones were obtained in high optical purity and in favor of the trans isomer (see A). Depending on the reaction partner, also cyclohexanones containing all-carbon quaternary centers (see B) as well as bicyclic scaffolds (see C) can be constructed with high efficiency.