title: Highly enantioselective michael addition of cyclic 1,3-dicarbonyl compounds to alpha,beta-unsaturated ketones.
abstract: [reaction: see text] The highly enantioselective Michael addition of 1,3-cyclic dicarbonyl compounds to alpha,beta-unsaturated ketones was reported to be catalyzed by an organic primary amine derived from quinine. A chiral anticoagulant drug, (S)-warfarin, was directly prepared in 96% ee, and other related important adducts were also obtained in excellent enantioselectivity (89-99% ee).
authors.affiliation: Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province and Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, China.
authors.forename: Jian-Wu
authors.initials: JW
authors.lastname: Xie
authors.forename: Lei
authors.initials: L
authors.lastname: Yue
authors.forename: Wei
authors.initials: W
authors.lastname: Chen
authors.forename: Wei
authors.initials: W
authors.lastname: Du
authors.forename: Jin
authors.initials: J
authors.lastname: Zhu
authors.forename: Jin-Gen
authors.initials: JG
authors.lastname: Deng
authors.forename: Ying-Chun
authors.initials: YC
authors.lastname: Chen
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry; D000925:Anticoagulants / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D007659:Ketones / Q000737:chemistry*; D008956:Models, Chemical; D008958:Models, Molecular; D011803:Quinine / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000588:Amines; D000925:Anticoagulants; D007659:Ketones; D012997:Solvents; D011803:Quinine