A short route to access oxaspiro[<i>n</i>,3,3]propellanes
Youssef Nassar, Olivier Piva
Abstract
Novel access to oxaspiro[n,3,3]propellanes has been developed from bicyclic lactones directly prepared by a photochemical hydroxymethylation or alternatively by a three-step sequence. Thanks to the presence of additional hydroxy- and propargylic groups, a second cyclization catalyzed by silver or bismuth salts, led to the propellane structure which was finally transformed into spiranic derivatives by a Simmons-Smith reaction or condensation with α-ketoesters.
Topics & Concepts
PropellaneChemistrySequence (biology)Bicyclic moleculeBismuthCondensationStereochemistryCombinatorial chemistryOrganic chemistryThermodynamicsBiochemistryPhysicsAsymmetric Synthesis and CatalysisOrganic Chemistry Cycloaddition ReactionsOxidative Organic Chemistry Reactions