Title of article
Organic base catalyzed carbonyl allylation of methyl trifluoropyruvate with activated alkenes
Author/Authors
Fan Zhang، نويسنده , , Xiaojin Wang، نويسنده , , Chen-Xin Cai، نويسنده , , Jin-Tao Liu، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2009
Pages
4
From page
83
To page
86
Abstract
The carbonyl allylation of methyl trifluoropyruvate (MeTFP) with activated alkenes has been investigated in detail using organic bases as catalysts. Organic bases, such as DMAP, Et3N, DABCO, NMM, Et2NH, and quinine, could deprotonate the allylic hydrogen of activated alkenes and furnish nucleophilic species to undergo the addition reaction with methyl trifluoropyruvate and afford versatile homoallylic alcohols with CF3 group in excellent yields. The 19F NMR monitoring indicated that the isomerization induced by base gave two separable diastereoisomers in an equilibrium ratio of 1:3. The relative configuration of hydroxy and the neighboring alkyl group in the major diastereoisomer was determined as syn-configuration by X-ray diffraction analysis.
Keywords
homoallylic alcohol , Methyl trifluoropyruvate , Allylation , Organic base , Activated alkene
Journal title
Tetrahedron
Serial Year
2009
Journal title
Tetrahedron
Record number
1094938
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