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Enantioselective Ruthenium-Catalyzed Ring-Closing Metathesis

Organic Letters · 2001 · Vol. 3(20) · pp. 3225–3228

T. Jon Seiders✉(California Institute of Technology)D. William Ward(California Institute of Technology)Robert H. Grubbs(California Institute of Technology)

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Abstract

[reaction: see text] The first enantioselective ruthenium olefin metathesis catalysts have been prepared, and high enantiomeric excesses (up to 90%) are observed in the desymmetrization of achiral trienes. A model consistent with the stereochemical outcome of the reactions is described and suggests side-on olefin binding and reorganization of the halide ligands.

Synthetic Organic Chemistry Methods Organometallic Complex Synthesis and Catalysis Asymmetric Hydrogenation and CatalysisDesymmetrizationEnantioselective synthesisChemistryRutheniumOlefin metathesisMetathesisCatalysisSalt metathesis reactionEnantiomerOlefin fiber