TITLE

Radical addition to ynol ethers � A convenient procedure for the stereoselective preparation of a-iodo enol ethers in neutral conditions

AUTHOR(S)
Longpr�, Fanny; Rusu, Natalia; Larouche, Maxime; Hanna, Rana; Daoust, Benoit
PUB. DATE
October 2008
SOURCE
Canadian Journal of Chemistry;Oct2008, Vol. 86 Issue 10, p970
SOURCE TYPE
Academic Journal
DOC. TYPE
Article
ABSTRACT
a-Iodo enol ethers, precursors of acyl anion equivalents, are not easily prepared. Herein we report that addition of activated iodoalkanes to ynol ethers under mild and neutral radical reaction conditions leads to a-iodo enol ethers in moderate to excellent yields with high stereoselectivity. The reaction can be carried out in various solvents at different temperatures. The methodology allows the preparation of �-alkylated and �,�-dialkylated a-iodo enol ethers. Reduction of the carbon-iodine bond of these species leads to the corresponding enol ethers with good yields.
ACCESSION #
34665680

 

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