Rubottom oxidation

The Rubottom oxidation is the chemical reaction of enolsilanes with m-chloroperoxybenzoic acid to give silyl-protected α-hydroxy ketones.



Reaction mechanism
Oxidation of the enolsilane (1) with m-chloroperoxybenzoic acid initially gives an epoxysilane (2). Rearrangement through a zwitterionic intermediate (3) gives the desired α-hydroxy ketone (4).