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Updated: Jan 20, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Bromoacetate Olefination Protocol for Norbixin and Julia-Kocienski Olefination for Its Ester Syntheses
Dahye Kim1, Mohammad Shariful Alam1, Wook-Jin Chung1
1Department of Energy Science and Technology and Department of Chemistry, Myongji University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do 17058, Korea.
Abstract:
A new olefination protocol utilizing ethyl bromoacetate was highlighted, in which magnesium enolate of the ester coupled with C20 dialdehyde 6, and double eliminations of the protected hydroxyl groups and bromine atoms of the coupling bromohydrin product, efficiently produced norbixin 1 after concomitant hydrolysis of the ester. A new (C7 + C10 + C7) disconnection approach was demonstrated for the synthesis of norbixin ethyl ester 2 by the Julia-Kocienski olefination of novel C7 benzothiazolyl-sulfone 11 and C10 2,7-dimethyl-2,4,6-octatrienedial (12).
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