Efficient Enantioselective Synthesis of Functionalized Tetrahydropyrans by Ru-Catalyzed Asymmetric Ring-Opening Metathesis/Cross-Metathesis (AROM/CM)
- 14 September 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (39) , 12288-12290
- https://doi.org/10.1021/ja0458672
Abstract
An efficient method for enantioselective synthesis of highly functionalized pyrans (up to 98% ee) through Ru-catalyzed asymmetric ring-opening metathesis/cross-metathesis is described. Reactions are promoted by a recyclable chiral Ru−chloride or a new chiral Ru−iodide complex; the latter catalyst is less efficient but gives rise to significantly higher levels of enantioselectivity. Catalytic reactions can be performed in undistilled solvent and with a wide range of substrates, including those that contain secondary and tertiary alcohols. Representative regioselective functionalizations that highlight the utility of the catalytic method are also presented.Keywords
This publication has 8 references indexed in Scilit:
- Synthesis of Oxygen- and Nitrogen-Containing Heterocycles by Ring-Closing MetathesisChemical Reviews, 2004
- Ru complexes bearing bidentate carbenes: from innocent curiosity to uniquely effective catalysts for olefin metathesisOrganic & Biomolecular Chemistry, 2003
- Ring‐Opening Cross‐MetathesesPublished by Wiley ,2003
- A fully stereocontrolled total synthesis of (+)-leucascandrolide ATetrahedron, 2003
- Catalytic Asymmetric Synthesis of Both syn- and anti-3,5-Dihydroxy Esters: Application to 1,3-Polyol/α-Pyrone Natural Product SynthesisOrganic Letters, 2003
- A Recyclable Chiral Ru Catalyst for Enantioselective Olefin Metathesis. Efficient Catalytic Asymmetric Ring-Opening/Cross Metathesis in AirJournal of the American Chemical Society, 2002
- Efficient and Recyclable Monomeric and Dendritic Ru-Based Metathesis CatalystsJournal of the American Chemical Society, 2000
- A Recyclable Ru-Based Metathesis CatalystJournal of the American Chemical Society, 1999