title: Iridium-catalyzed asymmetric hydrogenation of α-substituted α,β-unsaturated acyclic ketones: enantioselective total synthesis of (-)-mesembrine.
abstract: A highly efficient asymmetric hydrogenation of α-substituted α,β-unsaturated acyclic ketones catalyzed by chiral spiro iridium complexes for the preparation of chiral 2-substituted allylic alcohols has been developed (ee up to 99.7%). This method provides a concise route to (-)-mesembrine (34% yield, 12 steps).
authors.affiliation: State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China.
authors.forename: Qian-Qian
authors.initials: QQ
authors.lastname: Zhang
authors.forename: Jian-Hua
authors.initials: JH
authors.lastname: Xie
authors.forename: Xiao-Hui
authors.initials: XH
authors.lastname: Yang
authors.forename: Jian-Bo
authors.initials: JB
authors.lastname: Xie
authors.forename: Qi-Lin
authors.initials: QL
authors.lastname: Zhou
mesh_terms: D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006865:Hydrogenation; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007495:Iridium / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D020005:Propanols / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D026121:Indole Alkaloids; D007659:Ketones; D020005:Propanols; C006463:allyl alcohol; D007495:Iridium; C011300:mesembrine