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Methanesulfonamide: a Cosolvent and a General Acid Catalyst in Sharpless Asymmetric Dihydroxylations

Mikko H. Junttila and Osmo O. E. Hormi*

*Department of Chemistry, University of Oulu, P.O. Box 3000, FIN-90014 Oulu, Finland, Email: osmo.hormioulu.fi

M. H. Junttila, O. O. E. Hormi, J. Org. Chem., 2009, 74, 3038-3047.

DOI: 10.1021/jo8026998 (free Supporting Information)


Abstract

In Sharpless dihydroxylations of long chain olefins, methanesulfonamide is a cosolvent that aids in the transfer of the hydroxide ions from the water phase to the organic phase. In asymmetric dihydroxylations of conjugated aromatic olefins, the weakly acidic methanesulfonamide is a general acid catalyst that protonates the intermediate osmate esters.

see article for more examples

proposed phase transfer catalysis



Sodium Chlorite as an Efficient Oxidant and Hydroxy Ion Pump in Osmium-Catalyzed Asymmetric Dihydroxylation

M. H. Junttila, O. E. O. Hormi, J. Org. Chem., 2004, 69, 4816-4820.


Key Words

Sharpless Dihydroxylation


ID: J42-Y2009-1210