Organocatalytic Cloke–Wilson Rearrangement: Carbocation-Initiated Tandem Ring Opening/Cyclization of Cyclopropanes under Neutral Conditions
Guisheng Zhang, Liming Chen, Zhaokang Hu, Zhiguo Zhang, Jingjing Bi, Mengjuan Li, Xingjie Zhang
Abstract
We report a metal-, acid-, and base-free 2-(bromomethyl)naphthalene (2-BMN)-promoted organocatalytic Cloke-Wilson rearrangement of chain doubly activated cyclopropanes for the construction of 2,3-dihydrofurans via a carbocation-initiated tandem intramolecular ring-opening/recyclization process. The strategy is especially suitable for the construction of furan units in complex molecules, providing a solution to the problem of heavy-metal residues in dihydrofuran-containing drugs synthesized by traditional metal-based protocols. Thus, it is of potential interest in synthetic and medicinal chemistry.
Topics & Concepts
CarbocationIntramolecular forceChemistryRing (chemistry)TandemFuranStereochemistryNaphthaleneMedicinal chemistryOrganic chemistryMaterials scienceComposite materialCyclopropane Reaction MechanismsCatalytic Alkyne ReactionsCatalytic C–H Functionalization Methods