Organocatalyzed Protecting-Group-Free Total Synthesis of (<i>S,S</i>)- and (<i>S,R</i>)‑Reboxetine, an Antidepressant Drug

An efficient, simple, and concise organocatalyzed protecting-group-free synthetic approach to the stereoisomers of the antidepressant drug reboxetine and its implementation toward the asymmetric synthesis of (S,S)-reboxetine and (S,R)-reboxetine from commercially available trans-cinnamaldehyde are described. The synthesis features organocatalytic Jørgensen asymmetric epoxidation, epoxide migration, and Mitsunobu inversion as key steps.