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

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.