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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Bibliographic Details
Published in:Journal of organic chemistry 1996-12, Vol.61 (26), p.9111-9114
Main Authors: Bégué, Jean-Pierre, Bonnet-Delpon, Danièle, Bouvet, Denis, Rock, Michael H
Format: Article
Language:English
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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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo961356p