title: Copper(II)-catalyzed enantioselective hydrosilylation of halo-substituted alkyl aryl and heteroaryl ketones: asymmetric synthesis of (R)-fluoxetine and (S)-duloxetine.
abstract: A set of reaction conditions has been established to facilitate the non-precious copper-catalyzed enantioselective hydrosilylation of a number of structurally diverse β-, γ- or ε-halo-substituted alkyl aryl ketones and α-, β- or γ-halo-substituted alkyl heteroaryl ketones under air to afford a broad spectrum of halo alcohols in high yields and good to excellent enantioselectivities (up to 99% ee). The developed procedure has been successfully applied to the asymmetric synthesis of antidepressant drugs (R)-fluoxetine and (S)-duloxetine, which highlighted its synthetic utility.
authors.affiliation: College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 310036, China. jingwubc@hznu.edu.cn l_shijun@hznu.edu.cn.
authors.forename: Ji-Ning
authors.initials: JN
authors.lastname: Zhou
authors.forename: Qiang
authors.initials: Q
authors.lastname: Fang
authors.forename: Yi-Hu
authors.initials: YH
authors.lastname: Hu
authors.forename: Li-Yao
authors.initials: LY
authors.lastname: Yang
authors.forename: Fei-Fei
authors.initials: FF
authors.lastname: Wu
authors.forename: Lin-Jie
authors.initials: LJ
authors.lastname: Xie
authors.forename: Jing
authors.initials: J
authors.lastname: Wu
authors.forename: Shijun
authors.initials: S
authors.lastname: Li
mesh_terms: D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D000068736:Duloxetine Hydrochloride; D005473:Fluoxetine / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D007659:Ketones; D009942:Organometallic Compounds; D013876:Thiophenes; D005473:Fluoxetine; D003300:Copper; D000068736:Duloxetine Hydrochloride