A Widely Applicable and Versatile Method for the Ring‐Opening 1,3‐Carbocarbonation of Donor‐Acceptor Cyclopropanes
Heinrich F. von Köller, Peter G. Jones, Daniel B. Werz
Abstract
Abstract A 1,3‐carbocarbonation of 2‐substituted cyclopropane 1,1‐dicarboxylates introduces various saturated or unsaturated carbon residues at the 1‐ and 3‐ position of the former three‐membered ring. Under copper catalysis, ring‐opening attack with a Grignard reagent proceeded smoothly; the intermediate was converted to the final product by reaction with appropriate carbon‐based electrophiles under basic conditions. As nucleophiles, Grignard reagents derived from sp 3 ‐, sp 2 ‐, and sp‐hybridized carbon residues were successfully employed, whereas various aliphatic bromides and EBX derivatives (for sp moieties) served as electrophiles.
Topics & Concepts
ElectrophileCyclopropaneNucleophileRing (chemistry)ReagentChemistryCatalysisAcceptorCarbon fibersCombinatorial chemistryGrignard reagentMedicinal chemistryOrganic chemistryMaterials sciencePhysicsCondensed matter physicsComposite numberComposite materialCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsCatalytic Alkyne Reactions