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

0367581 - ÚOCHB 2012 RIV DE eng J - Journal Article
Boltukhina, Ekaterina - Sheshenev, Andrey - Lyapkalo, Ilya
Chemoselective Activation of Trimethylsilyl Enol Ether Functionalities in the Presence of Silyl-Protected Alcohols by Trimethylsilyl-Nonaflyl Exchange.
Synthesis. -, č. 21 (2011), s. 3507-3515. ISSN 0039-7881. E-ISSN 1437-210X
Institutional research plan: CEZ:AV0Z40550506
Keywords : biphasic catalysis * crown ether * sulfonylating reagent * trialkylsilyl ethers * alkenyl nonaflates
Subject RIV: CC - Organic Chemistry
Impact factor: 2.466, year: 2011

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.
Permanent Link: http://hdl.handle.net/11104/0202205