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[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.

Original publication

DOI

10.1021/ol070430v

Type

Journal article

Journal

Org Lett

Publication Date

26/04/2007

Volume

9

Pages

1725 - 1728

Keywords

Acylation, Amines, Hydroxylation, Molecular Structure, Oxidation-Reduction, Stereoisomerism