title: Kinetic Resolution of Benzylamines via Palladium(II)-Catalyzed C-H Cross-Coupling.
abstract: A Pd(II)-catalyzed enantioselective C-H cross-coupling of benzylamines via kinetic resolution has been achieved using chiral mono-N-protected α-amino-O-methylhydroxamic acid (MPAHA) ligands. Both chiral benzylamines and ortho-arylated benzylamines are obtained in high enantiomeric purity. The use of a readily removable nosyl (Ns) protected amino group as the directing group is a crucial practical advantage. Moreover, the ortho-arylated benzylamine products could be further transformed into chiral 6-substituted 5,6-dihydrophenanthridines as important structural motifs in natural products and bioactive molecules.
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Kai-Jiong
authors.initials: KJ
authors.lastname: Xiao
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Ling
authors.initials: L
authors.lastname: Chu
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Gang
authors.initials: G
authors.lastname: Chen
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Jin-Quan
authors.initials: JQ
authors.lastname: Yu
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D001596:Benzylamines / Q000737:chemistry*; D002384:Catalysis; D003432:Cross-Linking Reagents / Q000737:chemistry*; D015195:Drug Design; D006877:Hydroxamic Acids / Q000737:chemistry; D007700:Kinetics; D008024:Ligands; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D001596:Benzylamines; D003432:Cross-Linking Reagents; D006877:Hydroxamic Acids; D008024:Ligands; D010165:Palladium; C030796:benzylamine