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Issue 19, 2009
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Organocatalyzed highly stereoselective Michael addition of ketones to alkylidene malonates and nitroolefins using chiral primary-secondary diaminecatalysts based on bispidine

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Abstract

Organocatalysts containing primary-secondary diamines based on bispidine have been developed to catalyze the asymmetric Michael addition of ketones to alkylidene malonates and nitroalkenes. The corresponding products were obtained in high yields (up to 99%) with high diastereoselectivities (up to 99:1) and high enantioselectivities (up to 97% ee) under mild conditions using either environmentally benign water as the solvent or no solvent.

Graphical abstract: Organocatalyzed highly stereoselective Michael addition of ketones to alkylidene malonates and nitroolefins using chiral primary-secondary diamine catalysts based on bispidine

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Article information


Submitted
04 Jun 2009
Accepted
10 Jul 2009
First published
10 Aug 2009

Org. Biomol. Chem., 2009,7, 4120-4127
Article type
Paper

Organocatalyzed highly stereoselective Michael addition of ketones to alkylidene malonates and nitroolefins using chiral primary-secondary diamine catalysts based on bispidine

J. Liu, Z. Yang, X. Liu, Z. Wang, Y. Liu, S. Bai, L. Lin and X. Feng, Org. Biomol. Chem., 2009, 7, 4120
DOI: 10.1039/B910939K

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