Journal
ORGANIC LETTERS
Volume 10, Issue 24, Pages 5589-5591Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol802451e
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- National Science Foundation [CME-0809683]
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A simple yet efficient approach to various functionalized quaternary alpha-alkynyl alpha-fluoro esters and gamma-iodoallenoates from readily available allenoates through an alkynyl enolate intermediate generated by LDA is presented. Reaction of this alkynyl enolate with NFSI gives the alpha-product (alpha-alkynyl-alpha-fluoro ester), whereas the reaction of the silyl ether of alkynyl enolate with I-2 gives solely the gamma-product (iodoallenoate).
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