Download PDF
Synfacts 2011(5): 0562-0562  
DOI: 10.1055/s-0030-1259859
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

An Intermolecular Organocatalytic Entry to 4-Nitrocyclohexanones

Contributor(s): Benjamin List, Lars Ratjen
B. Wu, G.-G. Liu, M.-Q. Li, Y. Zhang, S.-Y. Zhang, J.-R. Qiu, X.-P. Xu, S.-J. Ji*, X.-W. Wang*
Soochow University, Suzhou, P. R. of China
Further Information

Publication History

Publication Date:
15 April 2011 (online)

    Permissions and Reprints

Significance

The two-component synthesis of substituted cyclohexanones by an organocatalyzed [5+1] double-Michael addition cascade is reported. The first step of the cascade, the reaction of pentadienones and nitromethane, is catalyzed by a bifunctional cinchona alkaloid of type 1. The isolated intermediate was then cyclized with a catalytic amount of base, such as KOH or DBU, affording the reaction products in good yields and stereoselectivities. The one-pot procedure involving the base-catalyzed cyclization without an intermediate workup was also successful; however, the products were obtained with slightly diminished stereoselectivities.