1610456-01-3Relevant academic research and scientific papers
PdII-Catalyzed Enantioselective C(sp3)?H Activation/Cross-Coupling Reactions of Free Carboxylic Acids
Hu, Liang,Shen, Peng-Xiang,Shao, Qian,Hong, Kai,Qiao, Jennifer X.,Yu, Jin-Quan
, p. 2134 - 2138 (2019)
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.
Palladium(II)-catalyzed enantioselective C(sp3)-H activation using a chiral hydroxamic acid ligand
Xiao, Kai-Jiong,Lin, David W.,Miura, Motofumi,Zhu, Ru-Yi,Gong, Wei,Wasa, Masayuki,Yu, Jin-Quan
supporting information, p. 8138 - 8142 (2014/06/23)
An enantioselective method for Pd(II)-catalyzed cross-coupling of methylene β-C(sp3)-H bonds in cyclobutanecarboxylic acid derivatives with arylboron reagents is described. High yields and enantioselectivities were achieved through the development of chiral mono-N-protected α-amino-O- methylhydroxamic acid (MPAHA) ligands, which form a chiral complex with the Pd(II) center. This reaction provides an alternative approach to the enantioselective synthesis of cyclobutanecarboxylates containing α-chiral quaternary stereocenters. This new class of chiral catalysts also show promises for enantioselective β-C(sp3)-H activation of acyclic amides.
