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

A metal-free protocol for the synthesis of substituted 1,6-dihydropyridines with quaternary stereogenic centers via a cascade aza-Wittig/6 pi-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.

Automated summary

A metal-free protocol for the synthesis of substituted 1,6-dihydropyridines with quaternary stereogenic centers has been developed, demonstrating high functional group compatibility and broad scope. Modification of products allows for increased complexity and chemical diversity, with attempts at asymmetric synthesis shown.