Pyrrolidine-ureas as bifunctional organocatalysts for asymmetric Michael addition of ketone to nitroalkenes: unexpected hydrogen bonding effect |
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| Authors: | Xiao-Yu Cao Jun-Cheng Zheng Zhen-Cao Shu Bi-Qin Wang |
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| Affiliation: | a State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, Chinab College of Chemistry and Materials Science, Sichuan Normal University, Chengdu 610066, China |
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| Abstract: | ![]()
A series of pyrrolidine-urea bifunctional organocatalysts was efficiently synthesized and applied to the asymmetric Michael addition of ketone to nitroolefin. Theoretical study was performed to shed light on the origin of their different activities and revealed that the rigid structure formed between catalyst 1b with nitroolefin via double hydrogen bonding retarded the approach of nucleophilic enamine intermediate. |
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| Keywords: | Pyrrolidine-urea Bifunctional Organocatalyst Michael addition Nitroalkene |
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