title: Chiral phosphoproline-catalyzed asymmetric Michael addition of ketones to nitroolefins: an experimental and theoretical study.
abstract: A novel pyrrolidine-based chiral phosphoproline is an effective bifunctional organocatalyst for the asymmetric Michael addition of ketones to nitroolefins giving high levels of diastereo- and enantio-selectivities (up to > 99 : 1 dr and 96% ee). anti-SR Transition state has the lowest barrier which controls the stereoselectivity, in agreement with experimental results.
authors.affiliation: Department of Chemistry and The Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, P. R. China.
authors.forename: Zhiping
authors.initials: Z
authors.lastname: Zeng
authors.forename: Ping
authors.initials: P
authors.lastname: Luo
authors.forename: Yao
authors.initials: Y
authors.lastname: Jiang
authors.forename: Yan
authors.initials: Y
authors.lastname: Liu
authors.forename: Guo
authors.initials: G
authors.lastname: Tang
authors.forename: Pengxiang
authors.initials: P
authors.lastname: Xu
authors.forename: Yufen
authors.initials: Y
authors.lastname: Zhao
authors.forename: G Michael
authors.initials: GM
authors.lastname: Blackburn
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D009574:Nitro Compounds / Q000138:chemical synthesis*; D010766:Phosphorylation; D011392:Proline / Q000031:analogs & derivatives*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D007659:Ketones; D009574:Nitro Compounds; D011392:Proline