Catalytic Generation of o-Quinone Dimethides by a Nondiazo Approach via Donor/Donor Platinum Carbenes

A platinum-catalyzed reaction of enynones with various dienophiles has been developed for the construction of tetrahydronaphthalene derivatives, which undergo a Diels-Alder reaction process with platinum carbenes and o-quinone dimethide (o-QDM) intermediates. In this protocol, an alkoxy-substituted conjugated enynone is used as a nondiazo carbene precursor for the generation of o-QDMs, thereby extending the methods available for the generation of o-QDMs. The reaction is characterized by its high atom economy, high diastereoselectivity, and broad substrate scope.