Chemoselective N-H insertion catalyzed by a de novo carbene transferase.

Abstract

The ability to perform organic reactions with chemoselectivity is of critical importance in synthesis. Recently, we reported that a de novo carbene transferase, a tetra-α-helical c-type heme-containing protein, C45, is proficient at N-H insertion reactions, proceeding via the intermolecular transfer of a metallocarbenoid intermediate into the N-H σ-bond to form a new N-C σ-bond. Here we demonstrate that C45 can also catalyse N-H insertion reactions chemoselectively, even when the substrate contains an unprotected hydroxyl group.