title: New atropisomeric amino alcohol ligands for enantioselective addition of diethylzinc to aldehydes.
abstract: Efficient synthesis of several new atropisomeric amino alcohols having 1-phenyl-1H-pyrrole skeleton are reported. Steric arrangements of the products were confirmed by a single-crystal X-ray measurement. The consequences of the size of the N-substituents on enantioinduction were examined by employing the enantioselective catalytic addition of diethylzinc to a series of substituted benzaldehydes (yields 91-97%, up to 85% enantiomeric excess). The special effect of the ortho methoxy group of the substrate on the enantioinduction is also interpreted.
authors.affiliation: Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary; MTA-BME Organic Chemical Technology Research Group, Hungarian Academy of Sciences, Budapest, Hungary.
authors.forename: F
authors.initials: F
authors.lastname: Faigl
authors.forename: Sz
authors.initials: S
authors.lastname: Deák
authors.forename: Zs
authors.initials: Z
authors.lastname: Erdélyi
authors.forename: T
authors.initials: T
authors.lastname: Holczbauer
authors.forename: M
authors.initials: M
authors.lastname: Czugler
authors.forename: M
authors.initials: M
authors.lastname: Nyerges
authors.forename: B
authors.initials: B
authors.lastname: Mátravölgyi
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000605:Amino Alcohols / Q000138:chemical synthesis*; D008024:Ligands; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000605:Amino Alcohols; D008024:Ligands; D009942:Organometallic Compounds; C454811:diethylzinc
keywords: amino alcohol; aromatic aldehyde; asymmetric catalysis; axial chirality; selective hydrolysis