Ketenedithioacetals as Surrogates for the Formal Insertion of Ketenes into Donor–Acceptor Cyclopropanes
Alexander Lücht, Alexander Kreft, Peter G. Jones, Daniel B. Werz
Abstract
The reactivity of donor–acceptor (D–A) cyclopropanes towards acceptor‐substituted ketenedithioacetals was investigated. In a Lewis‐acid‐catalyzed (3+2)‐cycloaddition, the corresponding dithiaspiro compounds were synthesized in good yields. The 1,3‐dithiane unit, a masked keto functionality, was cleaved by N ‐iodosuccinimide. Thus, this two‐step process represents a formal insertion of an acceptor‐substituted ketene into a D–A cyclopropane.
Topics & Concepts
ChemistryCyclopropaneLewis acids and basesKeteneDithianeReactivity (psychology)AcceptorCycloadditionStereochemistryMedicinal chemistryCatalysisCombinatorial chemistryOrganic chemistryRing (chemistry)PathologyPhysicsMedicineAlternative medicineCondensed matter physicsCyclopropane Reaction MechanismsCatalytic Alkyne ReactionsAsymmetric Synthesis and Catalysis