Kinetic resolution of protected alpha-amino acid derivatives by a chiral O-nucleophilic acyl transfer catalyst.
The kinetic resolution of alpha-trifluoroacetamido N-acyl oxazolidinethiones using 5-10% of the chiral, nonracemic O-nucleophilic acyl transfer catalyst 2 is described. A variety of substrates participate in this reaction in excellent yields, with s-factors ranging from 20 to 86.
Notte
Gregory T
GT
Department of Chemistry and Biochemistry, University of Colorado, Boulder, 80309-0215, USA.
Sammakia
Tarek
T
D000598:Amino Acids, Cyclic / Q000737:chemistry* / Q000302:isolation & purification; D002384:Catalysis; D006860:Hydrogen Bonding; D007094:Imides / Q000737:chemistry; D007700:Kinetics; D010080:Oxazoles / Q000737:chemistry / Q000302:isolation & purification; D013237:Stereoisomerism; D013871:Thiones / Q000737:chemistry / Q000302:isolation & purification
D000598:Amino Acids, Cyclic; D007094:Imides; D010080:Oxazoles; D013871:Thiones; C064210:oxazolidine