Organic Letters 2009-04-02

Highly enantioselective synthesis of nitrocyclopropanes via organocatalytic conjugate addition of bromomalonate to alpha,beta-unsaturated nitroalkenes.

Yi-Ning Xuan, Shao-Zhen Nie, Li-Ting Dong, Jun-Min Zhang, Ming Yan

Index: Org. Lett. 11(7) , 1583-6, (2009)

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Abstract

Highly enantioselective synthesis of nitrocyclopropanes was achieved via the organocatalytic conjugate addition of dimethyl bromomalonate to nitroalkenes and the consequent intramolecular cyclopropanation. 6'-Demethyl quinine was found to be the efficient catalyst. Excellent enantioselectivities, diastereoselectivities, and good yields were obtained for a variety of aryl or heteroaryl nitroethylenes.