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DOI: 10.1055/s-0030-1260207
Chemoselective Activation of Trimethylsilyl Enol Ether Functionalities in the Presence of Silyl-Protected Alcohols by Trimethylsilyl-Nonaflyl Exchange
Publication History
Publication Date:
05 September 2011 (online)

Abstract
Trimethylsilyl enol ethers bearing trialkylsilyl-protected hydroxy groups were converted into synthetically valuable bifunctional alkenyl nonaflates under the action of nonafluorobutane-1-sulfonyl fluoride combined with potassium fluoride in the presence of catalytic amounts of dibenzo-18-crown-6. The methodology has been demonstrated for structurally diverse substrates possessing various trialkylsilyl-protected hydroxy groups which remained intact during the reaction course.
Key words
biphasic catalysis - crown ether - sulfonylating reagent - trialkylsilyl ethers - alkenyl nonaflates
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References
Current address: Department of Chemistry, Imperial College London, Exhibition Road, South Kensington, London SW7 2AZ, UK.
14Note: The procedure has been extended to the enol derivatives which are not accessible directly from the carbonyl precursors; see ref. 3c.
19Sulfonylation of the deprotected hydroxy group with NfF leads to the unstable tertiary nonaflate undergoing a number of elimination/carbocation rearrangements.