Enantioselective Michael Addition of Cyclohexanone to Nitroolefins
Catalyzed by a New Pyrrolidinyl-isosteviol Bifunctional Organocatalyst in
Water
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Published:2024-02
Issue:2
Volume:21
Page:149-154
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ISSN:1570-1786
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Container-title:Letters in Organic Chemistry
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language:en
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Short-container-title:LOC
Author:
Liu Yu-Xia1,
Xu Yuan-Yuan1,
Li Shuai1,
Pan Zi-Qing1,
Li Bing-Xue1,
Fan Zhao-Yang1
Affiliation:
1. School of Chemical and Dyeing Engineering, Henan University of Engineering, Zhengzhou, China
Abstract
Abstract:
A new pyrrolidinyl-isosteviol bifunctional organocatalyst was synthesized, which was applied
to catalyze the asymmetric Michael addition between cyclohexanone and nitroolefins. With 10
mol % of the organocatalyst, the reaction proceeded in water in high yields (up to 99%) with excellent
diastereoselectivities (anti/syn up to 98:2) and good enantioselectivities (up to 90% ee). The design of
the proline-isosteviol conjugates as organocatalysts was based on the crucial role of proline in the
formation of enamine. To sum up, a new pyrrolidinyl-isosteviol bifunctional organocatalyst was synthesized,
which could effectively catalyze the C-C formation reaction between a number of nitroolefins
and cyclohexanone.
Publisher
Bentham Science Publishers Ltd.
Subject
Organic Chemistry,Biochemistry