β‐Diazocarbonyl Compounds: Synthesis and their Rh(II)‐Catalyzed 1,3 C−H Insertions
Liyin Jiang, Zhaofeng Wang, Melanie Armstrong, Marcos G. Suero
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.
Topics & Concepts
Hypervalent moleculeElectrophileDiazoEnolIntramolecular forceChemistryCarbeneKetoneSilylationCatalysisReagentStereochemistryMedicinal chemistryCombinatorial chemistryOrganic chemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsCatalytic Alkyne Reactions