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Pd II ‐Catalyzed Enantioselective C(sp 3 )−H Activation/Cross‐Coupling Reactions of Free Carboxylic Acids
Author(s) -
Hu Liang,
Shen PengXiang,
Shao Qian,
Hong Kai,
Qiao Jennifer X.,
Yu JinQuan
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201813055
Subject(s) - enantioselective synthesis , stereocenter , chemistry , carboxylic acid , amine gas treating , catalysis , reagent , aryl , coupling reaction , organic chemistry , medicinal chemistry , stereochemistry , alkyl
Pd II ‐catalyzed enantioselective C(sp 3 )−H cross‐coupling of free carboxylic acids with organoborons has been realized using either mono‐protected amino acid (MPAA) ligands or mono‐protected aminoethyl amine (MPAAM) ligands. A diverse range of aryl‐ and vinyl‐boron reagents can be used as coupling partners to provide chiral carboxylic acids. This reaction provides an alternative approach to the enantioselective synthesis of cyclopropanecarboxylic acids and cyclobutanecarboxylic acids containing α‐chiral tertiary and quaternary stereocenters. The utility of this reaction was further demonstrated by converting the carboxylic acid into cyclopropyl amine without loss of optical activity.