Oxa-Nazarov Cyclization-Michael Addition Sequence for the Rapid Construction of Dihydrofuranones

The Nazarov cyclization has been established as a powerful tool in constructing cyclopentenone skeletons. In sharp contrast, oxa-Nazarov cyclization that affords dihydrofuranones, a new type of product, has been less explored. In this work, we report the I-2-catalyzed oxa-Nazarov cyclization-Michael addition cascade between vinyl alpha-diketones and enones. The protocol allows access to a range of functionalized dihydrofuranones with good to high yields, and diverse further transformations on the products have been achieved. Furthermore, the mechanistic studies reveal that the 1,2-hydride shift occurs simultaneously during the dihydrofuranone formation.

Automated summary

In this work, the I-2-catalyzed oxa-Nazarov cyclization-Michael addition cascade between vinyl alpha-diketones and enones has been developed, providing a range of functionalized dihydrofuranones with good to high yields. Further transformations on the products have also been achieved. Mechanistic studies reveal the simultaneous occurrence of 1,2-hydride shift during dihydrofuranone formation.