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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

Enantioselective Michael Addition of Cyclohexanone to Nitroolefins Catalyzed by a New Pyrrolidinyl-isosteviol Bifunctional Organocatalyst in Water

Author(s): Yu-Xia Liu*, Yuan-Yuan Xu, Shuai Li, Zi-Qing Pan, Bing-Xue Li and Zhao-Yang Fan

Volume 21, Issue 2, 2024

Published on: 22 September, 2023

Page: [149 - 154] Pages: 6

DOI: 10.2174/1570178620666230801141834

Price: $65

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.

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