β-Diazocarbonyl Compounds: Synthesis and their Rh(II)-Catalyzed 1,3 C-H Insertions

Abstract

Herein, we describe the first electrophilic diazomethylation of ketone silyl enol ethers with diazomethyl-substituted hypervalent iodine reagents that gives access to unusual β-diazocarbonyl compounds. The potential of this unexplored class of diazo compounds for the development of new reactions was demonstrated by the discovery of a rare Rh-catalyzed intramolecular 1,3 C-H carbene insertion that led to complex cyclopropanes with excellent stereocontrol.

Keywords: C−H insertion; Rh-carbenes; cyclopropanes; diazo compounds; hypervalent iodine reagents.