Dearomatization of 3-Nitroindoles Enabled Using Palladium-Catalyzed Decarboxylative [4 + 2] Cycloaddition of 2-Alkylidenetrimethylene Carbonates.

ABSTRACT

A dearomatization process of 3-nitroindoles enabled using palladium-catalyzed decarboxylative [4 + 2] cycloaddition of either 2-alkylidenetrimethylene carbonates or 2-(hydroxymethyl)-3-arylallyl carbonates has been developed, affording a wide range of indoline-fused tetrahydropyrans in good yields with excellent diastereoselectivities. This reaction features a wide substrate scope and mild conditions and represents the first example of the application of π-allyl palladium 1,4-[O,C]-dipole species for the dearomative cycloaddition of electron-deficient heteroarenes.