title: Stereoselective synthesis of norephedrine and norpseudoephedrine by using asymmetric transfer hydrogenation accompanied by dynamic kinetic resolution.
abstract: Each of the enantiomers of both norephedrine and norpseudoephedrine were stereoselectively prepared from the common, prochiral cyclic sulfamidate imine of racemic 1-hydroxy-1-phenyl-propan-2-one by employing asymmetric transfer hydrogenation (ATH) catalyzed by the well-defined chiral Rh-complexes, (S,S)- or (R,R)-Cp*RhCl(TsDPEN), and HCO(2)H/Et(3)N as the hydrogen source. The ATH processes are carried out under mild conditions (rt, 15 min) and are accompanied by dynamic kinetic resolution.
authors.affiliation: Bio-Organic Science Division, Korea Research Institute of Chemical Technology, P.O. Box 107, Yuseong, Daejeon 305-600, Korea. leehk@krict.re.kr
authors.forename: Hyeon-Kyu
authors.initials: HK
authors.lastname: Lee
authors.forename: Soyeong
authors.initials: S
authors.lastname: Kang
authors.forename: Eun Bok
authors.initials: EB
authors.lastname: Choi
mesh_terms: D002384:Catalysis; D006865:Hydrogenation; D007700:Kinetics; D056004:Molecular Dynamics Simulation; D015394:Molecular Structure; D010665:Phenylpropanolamine / Q000138:chemical synthesis* / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C005331:norpseudoephedrine; D010665:Phenylpropanolamine; D012238:Rhodium