Enantioselective Michael Addition of Cyclohexanone to NitroolefinsCatalyzed by a New Pyrrolidinyl-isosteviol Bifunctional Organocatalyst inWater

作者：Yuxia Liu, Yuanyuan Xu, Shuai Li, Zi-Qing Pan, Bingxue Li, Zhaoyang Fan · 发表于：Letters in Organic Chemistry · 年份：2023 · DOI：10.2174/1570178620666230801141834 · 被引用次数：5 · 研究领域：Asymmetric Synthesis and Catalysis、Chemical Synthesis and Analysis、Carbohydrate Chemistry and Synthesis

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.