Synthetic utility of a fluorine-facilitated Claisen rearrangement: a novel synthetic method for 2, 4-alkadienoic acids using 2, 2, 2-trifluoroethyl phenyl sulfoxide.
T Nakai, K Tanaka, K Ogasawara, N Ishikawa
Index: Nakai, Takeshi; Tanaka, Kiyoshi; Ogasawara, Kyo; Ishikawa, Nobuo Chemistry Letters, 1981 , p. 1289 - 1292
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Citation Number: 5
Abstract
A novel synthetic method for 2, 4-alkadienoic acids from allylic alcohols and 2, 2, 2- trifluoroethyl phenyl sulfoxide is described which involves the in situ Claisen rearrangement facilitated by the fluorine. This method was applied to the stereocontrolled synthesis of pellitorine, a natural insecticide.
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