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Highly stereocontrolled synthesis of (2e,4z)-dienic esters by alumina catalyst

✍ Scribed by Sadao Tsuboi; Toshihide Masuda; Hiroshi Makino; Akira Takeda

Publisher
Elsevier Science
Year
1982
Tongue
French
Weight
215 KB
Volume
23
Category
Article
ISSN
0040-4039

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✦ Synopsis

Thermal treatment of p-allenic esters (2) with alumina catalyst in aprotic solvents yielded (2E,&Z)-dienoic esters (3) in 57-87s yields with 91-100% stereoselectivity. p-Allenic esters 2, which are readily obtained from trialkyl orthoacetate and propargylic alcohols (I.)', can be converted to 2,4-dienoic esters by the prototropic rearrangement with basic or acidic catalysts.

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