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

[Image: see text] 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 usi...

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Detalles Bibliográficos
Autores principales: Polychronidou, Vasiliki, Krupp, Anna, Strohmann, Carsten, Antonchick, Andrey P.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8397428/
https://www.ncbi.nlm.nih.gov/pubmed/34291925
http://dx.doi.org/10.1021/acs.orglett.1c02099
Descripción
Sumario:[Image: see text] 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.