Synthesis of Hindered and Functionalized 1-CF3 Substituted Olefins via a Carbolithiation−Elimination−Metalation Cascade

Addition of organolithium reagents to trifluoromethyl enol ethers 1a − d and thio enol ethers 2a provided stereoselectively the corresponding trisubstituted fluoroalkenes 3a − d in 70−90% yields. The products could themselves react with organolithium reagents and undergo a vinyl metalation providing...

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Published inJournal of organic chemistry Vol. 61; no. 26; pp. 9111 - 9114
Main Authors Bégué, Jean-Pierre, Bonnet-Delpon, Danièle, Bouvet, Denis, Rock, Michael H
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 27.12.1996
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:Addition of organolithium reagents to trifluoromethyl enol ethers 1a − d and thio enol ethers 2a provided stereoselectively the corresponding trisubstituted fluoroalkenes 3a − d in 70−90% yields. The products could themselves react with organolithium reagents and undergo a vinyl metalation providing, after trapping with an electrophile, tetrasubstituted olefins in excellent yields and with stereoselectivity. This method can be applied to other fluoroalkyl enol ethers (Rf = C2F5). The product, tetrasubstituted olefin, can be obtained directly from enol ether with 2 equiv of reagent through a carbolithiation−elimination−metalation cascade.
Bibliography:istex:8F6B26D90E61E240B4EC0656343C268A3B748EAA
ark:/67375/TPS-8LMLR4SG-W
Abstract published in Advance ACS Abstracts, November 15, 1996.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo961356p