Dearomatization of 3-Nitroindoles Enabled Using Palladium-Catalyzed Decarboxylative [4 + 2] Cycloaddition of
Pei-Hao Dou1,2,3, Shu-Pei Yuan1,2,3, Yan Chen1,2,3
1National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
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.
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