Chiral phosphoric acid catalyzed enantioselective transfer deuteration of ketimines by use of benzothiazoline as a deuterium donor: synthesis of optically active deuterated amines.
By use of 2-deuterated benzothiazoline as a deuterium donor in combination with a chiral phosphoric acid, the transfer deuteration of ketimine and α-iminoester took place smoothly to give α-deuterated amines in high yields with excellent enantioselectivities. The remarkable kinetic isotope effect suggests that carbon-deuterium bond cleavage is the rate-determining step.
Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1 Mejiro, Toshima-ku, Tokyo 171-8588, Japan.
Tsubasa
T
Sakamoto
Keiji
K
Mori
Takahiko
T
Akiyama
D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D052160:Benzothiazoles / Q000737:chemistry*; D002384:Catalysis; D007097:Imines / Q000737:chemistry*; D007700:Kinetics; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010756:Phosphoric Acids / Q000737:chemistry*; D013237:Stereoisomerism
D000588:Amines; D052160:Benzothiazoles; D007097:Imines; D009570:Nitriles; D010756:Phosphoric Acids; C542835:ketimine; C058836:benzothiazoline