Ruthenium-Catalyzed Olefin Metathesis Double-Bond Isomerization Sequence

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Abstract

A novel ruthenium-catalyzed tandem ring-closing metathesis (RCM) double-bond isomerization reaction is described in this paper. The utility of this method for the efficient syntheses of five-, six-, and seven-membered cyclic enol ethers is demonstrated. It relies on the conversion of a metathesis-active ruthenium carbene species to an isomerization-active ruthenium−hydride species in situ. This conversion is achieved by using various additives. Scope and limitations of the different protocols are discussed, and some mechanistic considerations based on ³¹P and ¹H NMR spectroscopic studies are presented.

Citing Articles

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This article has been cited by 27 ACS Journal articles (5 most recent appear below).

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  Stereoselective Synthesis of Substituted Tetrahydropyrans via Domino Olefin Cross-Metathesis/Intramolecular Oxa-Conjugate Cyclization

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  An Unexpected Oxidation in the Generation of Cyclopenta[c]piperidines by Ring-Closing Metathesis

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