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Enantioselective Access to 1 H ‐Isoindoles with Quaternary Stereogenic Centers by Palladium(0)‐Catalyzed C−H Functionalization
Author(s) -
Grosheva Daria,
Cramer Nicolai
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201809173
Subject(s) - stereocenter , enantioselective synthesis , chemistry , palladium , nucleophile , electrophile , catalysis , steric effects , surface modification , combinatorial chemistry , organic chemistry
A catalytic enantioselective method for the synthesis of chiral 1 H ‐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 1 H ‐isoindoles in high yields and enantioselectivities. The subsequent diastereoselective addition of nucleophiles provides access to densely substituted and sterically hindered isoindolines.