Pd^II -Catalyzed Enantioselective C(sp³ )-H Activation/Cross-Coupling Reactions of Free Carboxylic Acids.

ABSTRACT: Pd^II -catalyzed enantioselective C(sp³ )-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.

SUBMITTER: Hu L 

PROVIDER: S-EPMC6641982 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature