Pyrrolidine-ureas as bifunctional organocatalysts for asymmetric Michael addition of ketone to nitroalkenes: unexpected hydrogen bonding effect

Autor:	Yong Tang, Xiu-Li Sun, Jun-Cheng Zheng, Bi-Qin Wang, Zhen-Cao Shu, Yuxue Li, Xiao-Yu Cao
Rok vydání:	2010
Předmět:	chemistry.chemical_classification Ketone Organic Chemistry Enantioselective synthesis Nitroalkene Biochemistry Pyrrolidine Enamine chemistry.chemical_compound chemistry Nucleophile Drug Discovery Polymer chemistry Michael reaction Organic chemistry Bifunctional
Zdroj:	Tetrahedron. 66:9703-9707
ISSN:	0040-4020
DOI:	10.1016/j.tet.2010.10.038
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::ec76e2386bc372557a768b297b5fba83 https://doi.org/10.1016/j.tet.2010.10.038 Zobrazit plný text záznamu Full Text from ScienceDirect