Short enantioselective total synthesis of (+)-tofacitinib

[Display omitted] •An organocatalytic route for (+)-tofacitinib is described.•l-Proline catalysed hydroxylation is the key step.•Diastereoselective hydrogenation used for key intermediate.•(+)-Tofacitinib obtained in 8 step with 22.4% overall yield and 96.8% ee. An enantioselective total synthesis of Tofacitinib (CP-690,550), a Janus tyrosine kinase (JAK3) specific inhibitor has been achieved from the readily available 4-piperidone. Proline catalysed hydroxylation is the key step for the synthesis of enantiopure 1-benzyl-4-methylpiperidin-3-ol.