title: Organocatalytic asymmetric Michael-type/Wittig reaction of phosphorus ylides: synthesis of chiral α-methylene-δ-ketoesters.
abstract: An asymmetric Michael-type reaction of phosphorus ylides and α,β-unsaturated ketones under the catalysis of a chiral ion pair catalyst has been described. The ion pair catalyst containing a chiral counteranion was prepared by simply mixing 9-amino-(9-deoxy)-epi-quinine with l-N-Boc-proline. The optically active α-methylene-δ-ketoesters could be obtained with good to excellent enantioselectivities (up to 95% ee) under mild reaction conditions.
authors.affiliation: School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing, 210093, China.
authors.forename: Aijun
authors.initials: A
authors.lastname: Lin
authors.forename: Junying
authors.initials: J
authors.lastname: Wang
authors.forename: Haibin
authors.initials: H
authors.lastname: Mao
authors.forename: Huiming
authors.initials: H
authors.lastname: Ge
authors.forename: Renxiang
authors.initials: R
authors.lastname: Tan
authors.forename: Chengjian
authors.initials: C
authors.lastname: Zhu
authors.forename: Yixiang
authors.initials: Y
authors.lastname: Cheng
mesh_terms: D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis*; D007659:Ketones / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010758:Phosphorus / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D004952:Esters; D007659:Ketones; D010758:Phosphorus