title: Palladium(II)-catalyzed enantioselective C(sp³)-H activation using a chiral hydroxamic acid ligand.
abstract: An enantioselective method for Pd(II)-catalyzed cross-coupling of methylene β-C(sp(3))-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(sp(3))-H activation of acyclic amides.
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 N. Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Kai-Jiong
authors.initials: KJ
authors.lastname: Xiao
authors.forename: David W
authors.initials: DW
authors.lastname: Lin
authors.forename: Motofumi
authors.initials: M
authors.lastname: Miura
authors.forename: Ru-Yi
authors.initials: RY
authors.lastname: Zhu
authors.forename: Wei
authors.initials: W
authors.lastname: Gong
authors.forename: Masayuki
authors.initials: M
authors.lastname: Wasa
authors.forename: Jin-Quan
authors.initials: JQ
authors.lastname: Yu
mesh_terms: D000577:Amides / Q000737:chemistry; D001896:Boron Compounds / Q000737:chemistry; D002384:Catalysis; D003503:Cyclobutanes / Q000737:chemistry; D006877:Hydroxamic Acids / Q000737:chemistry*; D008024:Ligands; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000577:Amides; D001896:Boron Compounds; D003503:Cyclobutanes; D006877:Hydroxamic Acids; D008024:Ligands; D010165:Palladium