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Palladium(II)-Catalyzed Enantioselective C(sp3)–H Activation Using a Chiral Hydroxamic Acid Ligand

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journal contribution
posted on 17.12.2015, 02:24 by Kai-Jiong Xiao, David W. Lin, Motofumi Miura, Ru-Yi Zhu, Wei Gong, Masayuki Wasa, Jin-Quan Yu
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.