Auxiliary-Directed Pd-Catalyzed gamma-C(sp(3))-H Bond Activation of alpha-Aminobutanoic Acid Derivatives

作者：Pasunooti Kalyan Kumar; Banerjee Biplab; Yap Terence; Jiang Yaojia; Liu Chuan Fa^*

来源：Organic Letters, 2015, 17(24): 6094-6097.

DOI：10.1021/acs.orglett.5b03118

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 gamma-C(sp(3))-H bonds for C-C bond formation. Selective and efficient arylation and alkylation of several alpha-aminobutanoic acid derivatives led to various gamma-substituted non-natural amino acids. The MICA directing group can be conveniently removed and recovered under very mild conditions.

• 出版日期2015-12-18
• 单位南阳理工学院