Stereospecific substitution at alpha-carbon to trifluoromethyl group: application to optically active fluorinated amino acid syntheses.
This account summarizes how we performed the intramolecular nucleophilic substitutions of the hydroxy groups at alpha-position to trifluoromethyl group. The origin of the steric hindrance of the trifluoromethyl group was found to be the electrostatic repulsive force between the nucleophile and the negatively charged fluorine atoms.
Katagiri
Toshimasa
T
Department of Applied Chemistry, Faculty of Engineering, Okayama University, Okayama, Japan.
Uneyama
Kenji
K
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D005461:Fluorine; D007202:Indicators and Reagents; D015394:Molecular Structure; D013237:Stereoisomerism
D000596:Amino Acids; D007202:Indicators and Reagents; D005461:Fluorine