A General and Efficient Catalyst System for a Wacker-Type Oxidation Using TBHP as the Terminal Oxidant: Application to Classically Challenging Substrates
- 13 April 2009
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 131 (17), 6076-6077
- https://doi.org/10.1021/ja901212h
Abstract
Utilizing the rapidly synthesized Quinox ligand and commercially available aqueous TBHP, a Wacker-type oxidation has been developed, which efficiently converts the traditionally challenging substrate class of protected allylic alcohols to the corresponding acyloin products. Additionally, the catalytic system is general for several other substrate classes, converting terminal olefins to methyl ketones, with short reaction times. The system is scalable (20 mmol) and can be performed with a reduced catalyst loading of 1 mol%. Enantioenriched substrates undergo oxidation with complete retention of enantiomeric excess.Keywords
This publication has 15 references indexed in Scilit:
- Aldehydes from Pd-catalysed oxidation of terminal olefinsTetrahedron, 2007
- Recent Progress in Wacker Oxidations: Moving toward Molecular Oxygen as the Sole OxidantInorganic Chemistry, 2007
- An Intramolecular Diels−Alder Approach to the Eunicelins: Enantioselective Total Synthesis of Ophirin BJournal of the American Chemical Society, 2004
- The Wacker Reaction and Related Alkene Oxidation ReactionsCurrent Organic Chemistry, 2003
- Palladium(II)-Catalyzed Exchange and Isomerization Reactions. 17. Exchange of Chiral Allyl Alcohols with Hydroxide, Methoxide, and Phenyl at High [Cl-]. Stereochemistry of the Wacker ReactionThe Journal of Organic Chemistry, 1999
- Total Synthesis of Sarcodictyins A and BJournal of the American Chemical Society, 1998
- Complete Reverse Regioselection in Wacker Oxidation of Acetonides and Cyclic Carbonates of Allylic DiolsThe Journal of Organic Chemistry, 1995
- Chelation or Non‐Chelation Control in Addition Reactions of Chiral α‐ and β‐ Alkoxy Carbonyl Compounds [New Synthetic Methods (44)]Angewandte Chemie, 1984
- Synthetic Applications of the Palladium-Catalyzed Oxidation of Olefins to KetonesSynthesis, 1984
- Palladium(II) tert-butyl peroxide carboxylates. New reagents for the selective oxidation of terminal olefins to methyl ketones. The role of peroxymetalation in selective oxidative processesJournal of the American Chemical Society, 1980