Stereoselective synthesis of anti-alpha-(difluoromethyl)-beta-amino alcohols by boronic acid based three-component condensation. Stereoselective preparation of (2S,3R)-difluorothreonine.
Starting from optically active 3,3-difluorolactaldehyde, an alkenyl or aryl boronic acid, and an amine, a one-step three-component methodology was developed for the stereoselective preparation of anti-alpha-(difluoromethyl)-beta-amino alcohols. beta-Furyl-substituted anti-alpha-(difluoromethyl)-beta-amino alcohol was further elaborated to form (2S,3R)-difluorothreonine in high yield and ee.
Prakash
G K Surya
GK
Donald P. and Katherine B. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, University Park, Los Angeles, CA 90089-1661, USA. gprakash@usc.edu
Mandal
Mihirbaran
M
Schweizer
Stefan
S
Petasis
Nicos A
NA
Olah
George A
GA
D000605:Amino Alcohols / Q000138:chemical synthesis*; D001897:Boronic Acids / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013912:Threonine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
D000605:Amino Alcohols; D001897:Boronic Acids; D006845:Hydrocarbons, Fluorinated; C467958:difluorothreonine; D013912:Threonine