Tethered Aminohydroxylation: Dramatic Improvements to the Process
journal contributionposted on 26.04.2007 by Timothy J. Donohoe, Carole J. R. Bataille, William Gattrell, Johannes Kloesges, Emilie Rossignol
Any type of content formally published in an academic journal, usually following a peer-review process.
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.