title: Enantioselective addition of dialkylzinc to aromatic aldimines mediated by camphor-derived chiral β-amino alcohols.
abstract: The enantioselective addition of diethylzinc or dimethylzinc to N-(diphenylphosphinoyl)imines mediated by 1 or 2 could be achieved in high yields (70-97 %) and enantioselectivities (85-98 % ee). The catalytic loading of 1 or 2 a could be reduced to 10 mol % for methylation or ethylation of imines in high yields and enantioselectivities (79-96 %) when the reaction was conducted in the presence of 1.8 equiv of methanol. N-Monosubstituted amino alcohols induced higher enantioselectivity than their N,N-disubstituted congener in our catalytic system.
authors.affiliation: Department of Chemistry, National Tsing Hua University, Hsinchu 300 (Taiwan), Fax: (+886) 3-571-1082.
authors.forename: Wei-Ming
authors.initials: WM
authors.lastname: Huang
authors.forename: Biing-Jiun
authors.initials: BJ
authors.lastname: Uang
mesh_terms: D000605:Amino Alcohols / Q000737:chemistry*; D002164:Camphor / Q000737:chemistry*; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis*; D015394:Molecular Structure
chemical_list: D000605:Amino Alcohols; D006841:Hydrocarbons, Aromatic; D002164:Camphor
keywords: achiral additive; aldimine; dialkylzinc; enantioselective addition; synthetic methods; β-amino alcohol