Science of Synthesis

Suffert, J., Science of Synthesis, (2005) 26, 935.

Dimethyldioxirane in acetone is a useful oxidant that converts enolates into α-hydroxyl­ated carbonyl compounds ‌206‌.[‌181‌] The base used to form the enolates is often sodium hexamethyldisilazanide (NaHMDS) and, for example, when these reagents are applied to camphor the isomeric hydroxy ketones ‌207A‌ and ‌207B‌ are obtained in a ratio of 2:1 in 57% total yield. Oxaziridines, such as 2-phenylsulfonyloxaziridine, which are considerably less reactive than dioxiranes can still be used for the α-hydroxylation of electron-rich enolates (‌Scheme 96‌).[‌182‌]

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References

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• 8.Meeeee-Meee, (8888) M 88e, 8888.
• 8.Meeeee-Meee, (8888) M 88e, 8888.