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Diastereoselective michael addition of nitrogen and sulfur‐nucleophiles to α,β‐unsaturated δ‐thiolactams
Author(s) -
Sośnicki Jacek G.,
Jagodziński Tadeusz S.,
Liebscher Jürgen
Publication year - 1997
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570340249
Subject(s) - chemistry , michael reaction , reagent , nucleophile , adduct , piperidine , stereoselectivity , organic chemistry , methylhydrazine , sulfur , medicinal chemistry , phenylhydrazine , catalysis
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.