Synthesis of Eight-Membered Ring Compounds Using Enyne Metathesis
- 26 January 2000
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (4) , 543-545
- https://doi.org/10.1021/ol991398a
Abstract
A novel procedure for synthesizing eight-membered ring compounds was developed using ruthenium-catalyzed enyne metathesis. When a CH2Cl2 solution of enyne connected with catechol, o-amino phenol, or o-phenylenediamine was stirred in the presence of benzylidene ruthenium carbene complex (10 mol %) at room temperature overnight, an eight-membered ring compound was obtained in high yield. In a similar manner, monocyclic 1,4-diaza- or 1-oxa-4-azacyclooctene derivative was obtained in high yield.Keywords
This publication has 14 references indexed in Scilit:
- Total Synthesis of (-)-Stemoamide Using Ruthenium-catalyzed Enyne Metathesis ReactionHETEROCYCLES, 1997
- Enyne metathesis for the facile synthesis of highly functionalised novel bicyclic β-lactamsChemical Communications, 1997
- Total Synthesis of (−)-Stemoamide Using Ruthenium-Catalyzed Enyne Metathesis ReactionThe Journal of Organic Chemistry, 1996
- Catalytic Ring Closing Metathesis of Dienynes: Construction of Fused Bicyclic [n.m.0] RingsThe Journal of Organic Chemistry, 1996
- Catalytic Ring Closing Metathesis of Dienynes: Construction of Fused Bicyclic RingsJournal of the American Chemical Society, 1994
- Chromium-Catalyzed Intramolecular Enyne MetathesisOrganometallics, 1994
- Highly Selective Skeletal Reorganization of 1,6- and 1,7-Enynes to 1-Vinylcycloalkenes Catalyzed by [RuCl2(CO)3]2Journal of the American Chemical Society, 1994
- Ruthenium Catalyzed Enyne MetathesisSynlett, 1994
- The application of catalytic ring-closing olefin metathesis to the synthesis of unsaturated oxygen heterocyclesJournal of the American Chemical Society, 1992
- Metal-catalyzed rearrangement of alkene-alkynes and the stereochemistry of metallacyclobutene ring openingJournal of the American Chemical Society, 1985