PdII-Catalyzed Enantioselective C(sp3)−H Activation/Cross-Coupling Reactions of Free Carboxylic Acids
Liang Hu
Department of Chemistry, The Scripps Research Institute (TSRI), 10550 North Torrey Pines Road, La Jolla, CA, 92037 USA
Search for more papers by this authorPeng-Xiang Shen
Department of Chemistry, The Scripps Research Institute (TSRI), 10550 North Torrey Pines Road, La Jolla, CA, 92037 USA
Search for more papers by this authorDr. Qian Shao
Department of Chemistry, The Scripps Research Institute (TSRI), 10550 North Torrey Pines Road, La Jolla, CA, 92037 USA
Search for more papers by this authorDr. Kai Hong
Department of Chemistry, The Scripps Research Institute (TSRI), 10550 North Torrey Pines Road, La Jolla, CA, 92037 USA
Search for more papers by this authorDr. Jennifer X. Qiao
Discovery Chemistry, Bristol-Myers Squibb Company, P.O. Box 4000, Princeton, NJ, 08543 USA
Search for more papers by this authorCorresponding Author
Prof. Dr. Jin-Quan Yu
Department of Chemistry, The Scripps Research Institute (TSRI), 10550 North Torrey Pines Road, La Jolla, CA, 92037 USA
Search for more papers by this authorLiang Hu
Department of Chemistry, The Scripps Research Institute (TSRI), 10550 North Torrey Pines Road, La Jolla, CA, 92037 USA
Search for more papers by this authorPeng-Xiang Shen
Department of Chemistry, The Scripps Research Institute (TSRI), 10550 North Torrey Pines Road, La Jolla, CA, 92037 USA
Search for more papers by this authorDr. Qian Shao
Department of Chemistry, The Scripps Research Institute (TSRI), 10550 North Torrey Pines Road, La Jolla, CA, 92037 USA
Search for more papers by this authorDr. Kai Hong
Department of Chemistry, The Scripps Research Institute (TSRI), 10550 North Torrey Pines Road, La Jolla, CA, 92037 USA
Search for more papers by this authorDr. Jennifer X. Qiao
Discovery Chemistry, Bristol-Myers Squibb Company, P.O. Box 4000, Princeton, NJ, 08543 USA
Search for more papers by this authorCorresponding Author
Prof. Dr. Jin-Quan Yu
Department of Chemistry, The Scripps Research Institute (TSRI), 10550 North Torrey Pines Road, La Jolla, CA, 92037 USA
Search for more papers by this authorGraphical Abstract
Worth protecting: PdII-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.
Abstract
PdII-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.
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