Gold self-relay catalysis for accessing functionalized cyclopentenones bearing an all-carbon quaternary stereocenter

A new gold(i) self-relay catalysis consisting of a 3,3-rearrangement, Nazarov cyclization and Michael addition cascade of 1,3-enyne acetates with aurones and their derived azadienes is reported, and used to produce a series of densely functionalized cyclopentenones bearing a cyclic quaternary stereocenter in moderate to good yields under mild conditions. This tandem protocol demonstrates high regioselectivity, broad substrate flexibility and good functional group tolerance of substrates without inert atmosphere protection, providing a catalytic and convergent approach for creating all-carbon stereoscopic centers.

Automated summary

The new gold(I) self-relay catalysis reported involves a 3,3-rearrangement, Nazarov cyclization, and Michael addition cascade of 1,3-enyne acetates with aurones and their derived azadienes to produce densely functionalized cyclopentenones with a cyclic quaternary stereocenter. The tandem protocol shows high regioselectivity, broad substrate flexibility, and good functional group tolerance without the need for inert atmosphere protection, providing a catalytic and convergent approach for creating all-carbon stereoscopic centers.