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38.4.2.1.1.1 Variation 1: Reaction of Silyl Enol Ethers with Singlet Oxygen

DOI: 10.1055/sos-SD-038-00158

Scarso, A.; Strukul, G.Science of Synthesis, (200938145.

Ketene trimethylsilyl acetals 10, produced from the corresponding esters, undergo singlet oxygenation by reaction with molecular oxygen in the presence of tetraphenylporphyrin (TPP), leading, after silatropic rearrangement, to the corresponding α-(trimethylsilylperoxy) esters 11 in high yield (Scheme 4).[‌10‌‌12‌] Further desilylation with methanol at low temperatures releases the free α-hydroperoxy acid quantitatively.[‌10‌]

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