title: Auxiliary-Directed Pd-Catalyzed γ-C(sp(3))-H Bond Activation of α-Aminobutanoic Acid Derivatives.
abstract: New bidentate auxiliaries derived from the isoxazole-3-carboxamide and oxazole-4-carboxamide moieties were used for Pd-catalyzed C(sp(3))-H bond activation. The results show that, when placed on a primary amine compound, 5-methylisoxazole-3-carboxamide (MICA) directs Pd-catalyzed activation of inert γ-C(sp(3))-H bonds for C-C bond formation. Selective and efficient arylation and alkylation of several α-aminobutanoic acid derivatives led to various γ-substituted non-natural amino acids. The MICA directing group can be conveniently removed and recovered under very mild conditions.
authors.affiliation: School of Biological Sciences, Nanyang Technological University , Singapore 637551.
authors.forename: Kalyan Kumar
authors.initials: KK
authors.lastname: Pasunooti
authors.affiliation: School of Biological Sciences, Nanyang Technological University , Singapore 637551.
authors.forename: Biplab
authors.initials: B
authors.lastname: Banerjee
authors.affiliation: School of Biological Sciences, Nanyang Technological University , Singapore 637551.
authors.forename: Terence
authors.initials: T
authors.lastname: Yap
authors.affiliation: School of Biological Sciences, Nanyang Technological University , Singapore 637551.
authors.forename: Yaojia
authors.initials: Y
authors.lastname: Jiang
authors.affiliation: School of Biological Sciences, Nanyang Technological University , Singapore 637551.
authors.forename: Chuan-Fa
authors.initials: CF
authors.lastname: Liu
mesh_terms: D000613:Aminobutyrates / Q000737:chemistry*; D002384:Catalysis; D007555:Isoxazoles / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*
chemical_list: C000606655:5-methylisoxazole-3-carboxamide; D000613:Aminobutyrates; D007555:Isoxazoles; D010165:Palladium