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Tethered Aminohydroxylation:  Dramatic Improvements to the Process

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journal contribution
posted on 26.04.2007 by Timothy J. Donohoe, Carole J. R. Bataille, William Gattrell, Johannes Kloesges, Emilie Rossignol
Changing the identity of the N leaving group on a hydroxylamine-based reoxidant gives a dramatic improvement to the tethered aminohydroxylation reaction. Using OCOC6F5 as a leaving group means that only 1 mol % of osmium is required and yields as high as 98% can be obtained. Acyclic homoallylic alcohols were substrates considered too unreactive for effective use in the tethered aminohydroxylation reaction; improved reaction conditions mean that they have now become viable substrates for oxidation.