Highly Efficient Catalytic Asymmetric Epoxidation of Allylic Alcohols by an Oxovanadium-Substituted Polyoxometalate with a Regenerative TADDOL-Derived Hydroperoxide
- 8 February 2003
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 5 (5), 725-728
- https://doi.org/10.1021/ol027498p
Abstract
The oxovanadium(IV) sandwich-type POM catalyzes the chemo-, regio-, and stereoselective epoxidation of allylic alcohols by chiral hydroperoxides with very high catalytic efficiency (up to 42 000 TON), a potentially valuable oxidation for the development of sustainable processes. By using the sterically demanding, TADDOL-derived hydroperoxide TADOOH as the chiral oxygen source, enantiomeric ratios (er) of up to 95:5 have been achieved.Keywords
This publication has 9 references indexed in Scilit:
- The Chiral Switch of (S)-Metolachlor: A Personal Account of an Industrial Odyssey in Asymmetric CatalysisAdvanced Synthesis & Catalysis, 2002
- Homogeneous Catalysis for the Production of Fine Chemicals. Palladium- and Nickel-Catalysed Aromatic Carbon–Carbon Bond FormationTopics in Catalysis, 2002
- A Study of V-Pillared Layered Double Hydroxides as Catalysts for the Epoxidation of Terpenic Unsaturated AlcoholsJournal of Catalysis, 2001
- Preparation of TADOOH, a Hydroperoxide from TADDOL, and Use in Highly Enantioface- and Enantiomer-Differentiating OxidationsHelvetica Chimica Acta, 2001
- VAPO as catalyst for liquid phase oxidation reactions. Part II: stability of VAPO-5 during catalytic operationApplied Catalysis A: General, 1997
- Enthalpies of intramolecular etheration of saturated organolithium compounds in benzeneJournal of the American Chemical Society, 1986
- Introduction to Metal-Catalyzed OxidationsPublished by Elsevier ,1981
- Chiral hydroxamic acids as ligands in the vanadium catalyzed asymmetric epoxidation of allylic alcohols by tert-butyl hydroperoxideJournal of the American Chemical Society, 1977
- Electrophilic and nucleophilic organoselenium reagents. New routes to .alpha.,.beta.-unsaturated carbonyl compoundsJournal of the American Chemical Society, 1973