Synthesis of cis-fused cyclopentenone-pyrrolidine scaffolds via sequential aza-Piancatelli and Conia-ene type reactions in one pot.

A novel one-pot protocol that enables sequential execution of an aza-Piancatelli rearrangement and a Conia-ene type reaction has been developed under Lewis acid catalysis. Here, a combination of B(C6F5)3 and Cu(OTf)2, triethylamine, and triphenylphosphine yielded a wide range of cis-fused cyclopentenone-pyrrolidine scaffolds in one pot with good yields and diastereoselectivity.

Quaternary carbon construction through Piancatelli rearrangement: easy access to spirocyclopentenones.

A new and efficient approach to a series of novel multifunctionalized spirocyclopentenone scaffolds through Piancatelli rearrangement was developed under metal-free conditions. This method has been successfully applied to O-, N- and C-nucleophiles with excellent yields.

Cation Triggered Domino Aza-Piancatelli Rearrangement/Friedel-Crafts Alkylation of Indole-Tethered Furfuyl Alcohols to Access Cycloocta[b]indole Core of Alkaloids.

A domino approach to bridged cycloocta[b]indolone through a cascade of aza-Piancatelli rearrangement/Friedel-Crafts alkylation is developed. This transformation has been realized by reaction of an indole-tethered 2-furylcarbinol and substituted aniline in the presence of a Lewis acid to initiate aza-Piancatelli rearrangement followed by an in situ intramolecular Friedel-Crafts alkylation to access bridged tetracyclic frameworks in one pot.