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Synthesis 2011(21): 3507-3515  
DOI: 10.1055/s-0030-1260207
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Chemoselective Activation of Trimethylsilyl Enol Ether Functionalities in the Presence of Silyl-Protected Alcohols by Trimethylsilyl-Nonaflyl Exchange

Ekaterina V. Boltukhina, Andrey E. Sheshenev*, Ilya M. Lyapkalo
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nam. 2, 16610 Prague 6, Czech Republic
Fax: +44(20)75945804; e-Mail: a.sheshenev@imperial.ac.uk;
Further Information

Publication History

Received 1 July 2011
Publication Date:
05 September 2011 (online)

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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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1

Current address: Department of Chemistry, Imperial College London, Exhibition Road, South Kensington, London SW7 2AZ, UK.

14

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