Rubottom oxidation

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The Rubottom oxidation is the chemical reaction of enolsilanes with m-chloroperoxybenzoic acid to give silyl-protected α-hydroxy ketones.^[1][2][3]

[edit] 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).

[edit] References

1. ↑  Brook, A. G.; Macrae, D. M. J. Organometal. Chem. 1974, 77, C19.
2. ↑  Hassner, A.; Reuss, R. H.; Pinnick, H. W. J. Org. Chem. 1975, 40, 3427-3429. (DOI:10.1021/jo00911a027)
3. ↑  Rubottom, G. M. et al. Tetrahedron Lett. 1974, 4319.