Amine-Release Annulation of Enaminones: Bimetallic Co-Catalytic Synthesis of Cyclopentadienes from Alkynes

An efficient Au(III)/Ag(I) co-catalytic platform hasbeen establishedfor the synthesis of cyclopentadienes through amine-release annulationof enaminones with alkynes. Vinylcarbenoids that were generated from1,2-migration of propargyl esters may undergo a tandem annulationprocess with enaminones to give aminocyclopentenes as key intermediates.The bimetal catalytic system is compatible with a broad substratescope under mild reaction conditions. The obtained cyclopentadienesare allowed to undergo late-stage modifications into complex moleculeswith high chemo- and regioselectivities.

Automated summary

An efficient Au(III)/Ag(I) co-catalytic platform has been established for the synthesis of cyclopentadienes through amine-release annulation of enaminones with alkynes. The generated vinylcarbenoids undergo a tandem annulation process with enaminones to give aminocyclopentenes as key intermediates. This bimetal catalytic system is compatible with a broad substrate scope under mild reaction conditions, and the obtained cyclopentadienes can undergo late-stage modifications into complex molecules with high chemo- and regioselectivities.