SYNTHETIC UTILITY OF A FLUORINE-FACILITATED CLAISEN REARRANGEMENT: A NOVEL SYNTHETIC METHOD FOR 2,4-ALKANEDIENOIC ACIDS USING 2,2,2-TRIFLUOROETHYL PHENYL SULFOXIDE

DOI: 10.1246/cl.1981.1289

Source and publish data:

Chemistry Letters p. 1289 - 1292 (1981)

Update date:2022-08-05

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Authors:

Nakai, Takeshi

Tanaka, Kiyoshi

Ogasawara, Kyo

Ishikawa, Nobuo

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Article abstract of DOI:10.1246/cl.1981.1289

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.

Full text of DOI:10.1246/cl.1981.1289

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