First highly stereoselective synthesis of anti-alpha-trifluoromethyl-beta-amino acid derivatives.
The Reformatsky-type reaction of 2-bromo-3,3,3-trifluoropropanoic imide with various types of imines, in the presence of ZnBr2 as a Lewis acid in THF at 0 degrees C for 3 h, gave the corresponding alpha-trifluoromethyl-beta-amino acid derivatives in a highly anti-selective manner.
Shimada
Taichi
T
Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Matsugasaki, Kyoto 606-8585, Japan.
Yoshioka
Masamitsu
M
Konno
Tsutomu
T
Ishihara
Takashi
T
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D007094:Imides / Q000737:chemistry; D007097:Imines / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
D000596:Amino Acids; D007094:Imides; D007097:Imines