Open AccessCascade aza-Wittig/6π-Electrocyclization in the Synthesis of 1,6-Dihydropyridines
Author(s) -
Vasiliki Polychronidou,
Anna Krupp,
Carsten Strohmann,
Andrey P. Antonchick
Publication year - 2021
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.1c02099
Subject(s) - stereocenter , chemistry , wittig reaction , cascade , combinatorial chemistry , cascade reaction , compatibility (geochemistry) , stereochemistry , organic chemistry , enantioselective synthesis , catalysis , geochemistry , chromatography , geology
A metal-free protocol for the synthesis of substituted 1,6-dihydropyridines with quaternary stereogenic centers via a cascade aza-Wittig/6π-electrocyclization process has been developed. The high functional group compatibility and broad scope of this method were demonstrated by using a wide range of easily available vinyliminophosphoranes and ketones, with yields up to 97%. A modification of the obtained products allowed for an increase in complexity and chemical diversity. Finally, attempts for asymmetric synthesis of 1,6-dihydropyridines are demonstrated.