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

被引：0
|
作者：
Liu, Yu-Xia [1 ]
Xu, Yuan-Yuan [1 ]
Li, Shuai [1 ]
Pan, Zi-Qing [1 ]
Li, Bing-Xue [1 ]
Fan, Zhao-Yang [1 ]
机构：
[1] Henan Univ Engn, Sch Chem & Dyeing Engn, Zhengzhou, Peoples R China
来源：
LETTERS IN ORGANIC CHEMISTRY | 2024年 / 21卷 / 02期
基金：
中国国家自然科学基金;
关键词：
Isosteviol; L-proline; asymmetric catalysis; organocatalyst; Michael reaction; nitroalkenes; ASYMMETRIC ALDOL; ALPHA; ALPHA-DISUBSTITUTED ALDEHYDES; EFFICIENT; PROLINE; NITROALKENES; MANNICH;
D O I：
10.2174/1570178620666230801141834
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：149 / 154
页数：6
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