Lewis‐Acid‐Catalyzed (3+2)‐Cycloadditions of Donor‐Acceptor Cyclopropanes with Thioketenes
Grzegorz Mlostoń, Mateusz Kowalczyk, André U. Augustin, Peter G. Jones, Daniel B. Werz
Abstract
Abstract The reactivity of donor‐acceptor (D‐A) cyclopropanes towards thioketenes was investigated. In a (3+2)‐cycloaddition using Sc(OTf) 3 as a Lewis acidic catalyst, the corresponding exocyclic thioenol ethers (2‐methylidene tetrahydrothiophenes) were formed in moderate to good yields. Unsymmetrical thioketenes provided E / Z mixtures at the double bond, with the Z isomer being preferred.
Topics & Concepts
ChemistryLewis acids and basesCycloadditionCatalysisReactivity (psychology)AcceptorMedicinal chemistryDouble bondStereochemistryOrganic chemistryAlternative medicinePhysicsMedicineCondensed matter physicsPathologyCyclopropane Reaction MechanismsCatalytic Alkyne ReactionsOrganic Chemistry Cycloaddition Reactions