Work

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

Year: 2017

Type: article

Abstract: 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.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.7b01410

Authors: Santanu Panda, Joseph M. Ready

Institution: The University of Texas Southwestern Medical Center

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Welch Foundation, National Institutes of Health, National Institute of General Medical Sciences

Awards: G7073091334, Synthesis and Evaluation of Biologically Active Natural Products