The highly diastereoselective base-promoted intramolecular cyclization of a variety of enantiopure sulfinyl dienyl amines provides novel sulfinyl tetrahydropyridines that are readily converted to 3-hydroxy tetrahydropyridines via sigmatropic rearrangement. The influence of N- and C- substituents on the process has been studied. Procedures to shorten the sequence such as the tandem cyclization followed by [2,3]-sigmatropic rearrangement, as well as cyclization of the free amine, under Boc- or ArSO- deprotection conditions have been examined. Good to excellent levels of selectivity are generally observed for the reported transformations (dr: 75/25 to >98/2). A novel protocol to access substituted amino dienyl sulfoxides is also reported. ; This research was supported by MINECO (CTQ2013-46459- C2-2-P) and (CTQ2009-07752) cofunded by FEDER. We also thank CSIC for a contract to RHB (201080E101) and CSIC and Fondo Social Europeo for a JAE-doc contract to CS. LI thanks Comunidad de Madrid (Spain) for support (BIPEDD-2: S2010-BMD-2457). We are grateful to Dr. Carmen de la Torre (IQOG-CSIC) and Dr. Miguel Ángel Sierra (UCM) for encouragement and support. ; Peer Reviewed