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

Fan-Tao Meng, Jing-Long Chen, Xiao-Yan Qin, Tian-Shu Zhang,* Shu-Jiang Tu, Bo Jiang,* and Wen-Juan Hao*

A new gold(I) self-relay catalysis consisted of 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 the mild conditions. This tandem protocol demonstrates high regioselectivity, broad substrate flexibility and good functional group tolerance of substrates without inert atmosphere protection, rendering a catalytic and convergent approach to create all-carbon stereoscopic centers.

Org. Chem. Front. 2022, 9, 140-146; DOI: 10.1039/D1QO01313K