Silver-catalyzed cyclization of acetylenic alcohols and acids: a remarkable accelerating effect of a propargylic C–O bond

Concepts

Chemical EngineeringNovel OrganocatalystsOxanes 5EngineeringAlkene MetathesisNatural SciencesAcetylenic AlcoholsDiversity-oriented SynthesisFunctionalized HeterocyclesPropargylic C–o BondOrganic ChemistryOrganometallic CatalysisCatalysisChemistrySilver-catalyzed CyclizationHeterocycle ChemistryAsymmetric Catalysis

Abstract

The heteroannulation catalyzed by silver salts of alkynols 1, 2 or alkynoic acids 3 is considerably enhanced by the presence of a propargylic C–O bond. This method allows for a rapid access to highly functionalized heterocycles, such as α-methylene oxolanes 4 or oxanes 5 and as γ-methylene pentanolactones 6.

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