A Predictably Selective Aliphatic C–H Oxidation Reaction for Complex Molecule Synthesis

M. Christina White of the University of Illinois, Science 2007: Vol. 318. no. 5851, pp. 783 - 787.

1. although the yields are only moderate, selectivity is good. In all cases examined, hydroxylation occurred preferentially at the most electron-rich tertiary (3°) C–H bond, despite the fact that secondary (2°) C–H bonds have a significant statistical advantage (entries 1 to 9)
2. hydroxylation occurred with complete retention of stereochemistry (entries 6 and7)
3. This reagent showed substantial (probably steric) selectivity. Different from methyl(trifluoromethyl)dioxirane.