Stereoselective radical amination of electron-deficient C(sp3)-H bonds by Co(II)-based metalloradical catalysis: direct synthesis of α-amino acid derivatives via α-C-H amination.

Abstract

The cobalt(II) complex of 3,5-Di(t)Bu-IbuPhyrin, [Co(P1)], is an effective catalyst for intramolecular amination of electron-deficient C-H bonds, including those adjacent to electron-withdrawing CO(2)R, C(O)NR(2), C(O)R, and CN groups, in excellent yields with high regio- and stereoselectivity. The [Co(P1)]-catalyzed amination system provides a direct method for the synthesis of α-amino acid derivatives from the corresponding carboxylate precursors.