A facile stereocontrolled synthesis of anti-alpha-(trifluoromethyl)-beta-amino alcohols.
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.
Prakash
G K
GK
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
Mandal
M
M
Schweizer
S
S
Petasis
N A
NA
Olah
G A
GA
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
D000447:Aldehydes; D000605:Amino Alcohols; D001897:Boronic Acids; D010126:Ozone; D000171:Acrolein; C012843:cinnamaldehyde