Ionic Liquids as a Convenient New Medium for the Catalytic Asymmetric Dihydroxylation of Olefins Using a Recoverable and Reusable Osmium/Ligand

Luís C. Branco and Carlos A. M. Afonso*

*CQFM, Department of Chemical Engineering, Instituto Superior Técnico, 1049-001 Lisboa, Portugal, Email: carlosafonsoist.utl.pt

L. C. Branco, C. A. M. Afonso, J. Org. Chem., 2004, 69, 4381-4389.

DOI: 10.1021/jo035588h

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Abstract

The ionic liquids [C₄mim][PF₆] and [C₈mim][PF₆] as cosolvents in asymmetric dihydroxylation give yields and enantioselectivity comparable or higher than those of the conventional H₂O/tert-BuOH solvent system. After extraction of the reaction mixture with diethyl ether, the contamination of the product by osmium was remarkably low. The reuse of ionic liquid and catalyst is possible.

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Key Words

Sharpless Dihydroxylation, Osmium, NMO, Potassium Ferricyanide, Ionic Liquids

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ID: J42-Y2004-600