Diastereoselective Michael Addition of Nitrogen and Sulfur-Nucleophiles to α,β-Unsaturated δ-Thiolactams

Article abstract of DOI:10.1002/jhet.5570340249

5,6-Dihydropyridine-2-thiones 2 are synthesized from 5,6-dihydropyridin-2-ones 1 and Lawesson reagent. Stereoselective Michael-like addition of amines, methylhydrazine or functionalized thiols affords trans piperidine-2-thiones 5 with the corresponding heterosubstituent in position 4 as major products. The configuration of the adducts 5 was determined by nmr-techniques.