Cascade aza-Wittig/6π-Electrocyclization in the Synthesis of 1,6-Dihydropyridines | Zendy

Vasiliki Polychronidou | Zendy; Anna Krupp | Zendy; Carsten Strohmann | Zendy; Andrey P. Antonchick | Zendy

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Cascade 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.

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