Tethered aminohydroxylation: dramatic improvements to the process.
[reaction: see text] 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.
Donohoe
Timothy J
TJ
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK. timothy.donohoe@chem.ox.ac.uk
Bataille
Carole J R
CJ
Gattrell
William
W
Kloesges
Johannes
J
Rossignol
Emilie
E
D000215:Acylation; D000588:Amines / Q000737:chemistry*; D006900:Hydroxylation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000588:Amines