title: A facile stereocontrolled synthesis of anti-alpha-(trifluoromethyl)-beta-amino alcohols.
abstract: A short stereocontrolled preparation of anti-alpha-(trifluoromethyl)-beta-amino alcohols is described, involving an initial CF(3) transfer to cinnamaldehyde and a one-step, three-component condensation of 3,3,3-trifluorolactic aldehyde, an alkenyl (aryl) boronic acid, and an amine. Applying this methodology to chiral 3,3,3-trifluorolactic aldehyde allowed us to generate an amino alcohol enantioselectively in 92% ee.
authors.affiliation: Donald P. and Katherine B. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, University Park, Los Angeles, California 90089-1661, USA. prakash@methyl.usc.edu
authors.forename: G K
authors.initials: GK
authors.lastname: Prakash
authors.forename: M
authors.initials: M
authors.lastname: Mandal
authors.forename: S
authors.initials: S
authors.lastname: Schweizer
authors.forename: N A
authors.initials: NA
authors.lastname: Petasis
authors.forename: G A
authors.initials: GA
authors.lastname: Olah
mesh_terms: D000171:Acrolein / Q000031:analogs & derivatives / Q000737:chemistry; D000447:Aldehydes / Q000138:chemical synthesis*; D000605:Amino Alcohols / Q000138:chemical synthesis*; D001897:Boronic Acids / Q000737:chemistry; D010126:Ozone / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000605:Amino Alcohols; D001897:Boronic Acids; D010126:Ozone; D000171:Acrolein; C012843:cinnamaldehyde