Auxiliary-Directed Pd-Catalyzed γ-C(sp(3))-H Bond Activation of α-Aminobutanoic Acid Derivatives
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Published on: August 17, 2018
Kalyan Kumar Pasunooti1, Biplab Banerjee1, Terence Yap1
1School of Biological Sciences, Nanyang Technological University , Singapore 637551.
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.
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