title: Highly enantioselective phenylacetylene addition to aromatic ketones catalyzed by cinchona alkaloid-aluminum complexes.
abstract: The catalytic asymmetric addition of phenylacetylene to aromatic ketones is reported. The catalyst, generated from commercially available Cinchona alkaloids and industrially available triethylaluminum, gives the expected tertiary alcohols with good enantiomeric excess (70-89%) and yields (60-83%). No previous case has been reported successfully using triethylaluminum as a Lewis acid in the asymmetric alkynylation of carbonylic derivatives, and thus we provide a new method to obtain optically active tertiary propargyl alcohols.
authors.affiliation: Department of Biochemistry & Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou, Gansu 730000, China.
authors.forename: Lei
authors.initials: L
authors.lastname: Liu
authors.forename: Rui
authors.initials: R
authors.lastname: Wang
authors.forename: Yong-Feng
authors.initials: YF
authors.lastname: Kang
authors.forename: Chao
authors.initials: C
authors.lastname: Chen
authors.forename: Zhao-Qing
authors.initials: ZQ
authors.lastname: Xu
authors.forename: Yi-Feng
authors.initials: YF
authors.lastname: Zhou
authors.forename: Ming
authors.initials: M
authors.lastname: Ni
authors.forename: Hua-Qing
authors.initials: HQ
authors.lastname: Cai
authors.forename: Mao-Zhen
authors.initials: MZ
authors.lastname: Gong
mesh_terms: D000114:Acetylene / Q000031:analogs & derivatives* / Q000737:chemistry*; D000535:Aluminum / Q000737:chemistry* / Q000378:metabolism; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry* / Q000378:metabolism; D006841:Hydrocarbons, Aromatic / Q000737:chemistry / Q000378:metabolism; D007659:Ketones / Q000737:chemistry* / Q000378:metabolism; D013237:Stereoisomerism
chemical_list: D002930:Cinchona Alkaloids; D006841:Hydrocarbons, Aromatic; D007659:Ketones; C044736:phenylacetylene; D000535:Aluminum; D000114:Acetylene