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Issue 6, 2010
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Novel thiourea-amine bifunctional catalysts for asymmetric conjugate addition of ketones/aldehydes to nitroalkenes: rational structural combination for high catalytic efficiency

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Abstract

A series of thiourea-amine bifunctional catalysts have been developed by a rational combination of prolines with cinchona alkaloids, which are connected by a thiourea motif. The catalyst 3a, prepared from L-proline and cinchonidine, was found to be a highly efficient catalyst for the conjugate addition of ketones/aldehydes to a wide range of nitroalkenes (up to 98/2 dr and 96% ee). The privileged cinchonidine backbone and the thiourea motif are essential to the reaction activity and enantioselectivity.

Graphical abstract: Novel thiourea-amine bifunctional catalysts for asymmetric conjugate addition of ketones/aldehydes to nitroalkenes: rational structural combination for high catalytic efficiency

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Article information


Submitted
09 Dec 2009
Accepted
12 Jan 2010
First published
21 Jan 2010

Org. Biomol. Chem., 2010,8, 1275-1279
Article type
Communication

Novel thiourea-amine bifunctional catalysts for asymmetric conjugate addition of ketones/aldehydes to nitroalkenes: rational structural combination for high catalytic efficiency

J. Chen, Y. Cao, Y. Zou, F. Tan, L. Fu, X. Zhu and W. Xiao, Org. Biomol. Chem., 2010, 8, 1275
DOI: 10.1039/B925962G

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