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26.6.5.1.2.1 Variation 1: Oxidation with 3-Chloroperoxybenzoic Acid

DOI: 10.1055/sos-SD-026-00761

Suffert, J.Science of Synthesis, (200526941.

Silyl enol ethers 227 react rapidly and directly with 3-chloroperoxybenzoic acid to afford the siloxy epoxides 228 in good yields. Treatment of these products with acetic anhydride and triethylamine produces α-hydroxy ketones 229..[‌193‌] In a very similar two-step reaction treatment of the silyl enol ether 230 with 3-chloroperoxybenzoic acid, and desilylation with triethylammonium fluoride in dichloromethane gives the hydroxy ketone 231 in 83% yield (Scheme 103).[‌194‌]

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