Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

Palladium Catalyzed Asymmetric Three-Component Coupling of Boronic Esters, Indoles, and Allylic Acetates

Palladium Catalyzed Asymmetric Three-Component Coupling of Boronic Esters, Indoles, and Allylic Acetates
Joseph M. Ready, Santanu Panda
Boronic esters react with 2-lithiated indoles to form boronate intermediates. The boronate reacts with allylic acetates in the presence of (BINAP)Pd catalysts to allylate C3 concurrent with alkyl migration from B to C2 of the indole. Overall, the process is a three-component coupling that joins an allylic acetate, and indole and an organo-B(pin) species to provide substituted indoles and indolines with high enantio-, regio-, and diastereoselectivity.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b01410

DOI: 10.1021/jacs.7b01410

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