Enantioselective Access to 1H-Isoindoles with Quaternary Stereogenic Centers by Palladium(0)-Catalyzed C-H Functionalization

Angewandte Chemie
Daria Grosheva, Nicolai Cramer

Abstract

A catalytic enantioselective method for the synthesis of chiral 1H-isoindoles bearing quaternary stereogenic centers is reported. Powered by readily accessible phosphordiamidite ligands, the presented palladium(0)-catalyzed C-H functionalization uses trifluoroacetimidoyl chlorides as electrophilic components. It delivers previously inaccessible perfluoroalkylated 1H-isoindoles in high yields and enantioselectivities. The subsequent diastereoselective addition of nucleophiles provides access to densely substituted and sterically hindered isoindolines.

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Citations

Aug 9, 2020·Chemistry : a European Journal·Oleksandr VyhivskyiOlivier Baudoin
Aug 18, 2021·The Journal of Organic Chemistry·Chun-Tai HungCheng-Che Tsai
Jan 23, 2020·Journal of the American Chemical Society·Qui-Hien NguyenNicolai Cramer

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