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Synfacts 2009(10): 1154-1154  
DOI: 10.1055/s-0029-1217949
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Four-Component Cascade Reaction

Contributor(s): Benjamin List, Saihu Liao
F.-L. Zhang, A.-W. Xu, Y.-F. Gong*, M.-H. Wei, X.-L. Yang
Huazhong University of Science and Technology, Wuhan, P. R. of China
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Publication History

Publication Date:
22 September 2009 (online)

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Significance

The authors reported an elegant four-component cascade oxa-Michael-Michael-Michael-aldol condensation reaction. In a one-pot procedure with prolinol silyl ether (1) as catalyst, acrolein (2), alcohols 3, and nitroolefins 4 can be efficiently converted into highly functionalized ­cyclohexenes 5 containing three stereocenters in good yields and with almost perfect stereocontrol (er > 99.5:0.5, dr > 20:1) via an iminium-enamine-iminium-enamine catalysis sequence.