title: Dynamic kinetic resolution-based asymmetric transfer hydrogenation of 2-benzoylmorpholinones and its use in concise stereoselective synthesis of all four stereoisomers of the antidepressant reboxetine.
abstract: Dynamic kinetic resolution-driven, asymmetric transfer hydrogenation reaction of 2-benzoylmorpholin-3-ones (4) proceeds efficiently to give the corresponding (2R,3S)- or (2S,3R)-2-(hydroxyphenylmethyl)morpholin-3-ones (6) with an excellent level of diastereo- and enantioselectivity and simultaneous control of two contiguous stereogenic centers in a single step. This process is employed to prepare all four stereoisomers of the antidepressant reboxetine.
authors.affiliation: Bio-Organic Science Division, Korea Research Institute of Chemical Technology, PO Box 107, Yuseong, Daejeon 305-600, Korea.
authors.forename: Se-Mi
authors.initials: SM
authors.lastname: Son
authors.forename: Hyeon-Kyu
authors.initials: HK
authors.lastname: Lee
mesh_terms: D000928:Antidepressive Agents / Q000138:chemical synthesis* / Q000737:chemistry; D006865:Hydrogenation; D007700:Kinetics; D015394:Molecular Structure; D009025:Morpholines / Q000138:chemical synthesis / Q000737:chemistry*; D000077593:Reboxetine; D013237:Stereoisomerism; D013816:Thermodynamics
chemical_list: D000928:Antidepressive Agents; D009025:Morpholines; D000077593:Reboxetine