Highly regio- and stereoselective synthesis of 2(E),4-Alkadienoates via the Pd(0)-catalyzed reaction of aryl halides with 3,4-alkadienoates

Chunling Fu; Shengming Ma

doi:10.1021/ol0473389

Highly regio- and stereoselective synthesis of 2(E),4-Alkadienoates via the Pd(0)-catalyzed reaction of aryl halides with 3,4-alkadienoates

Org Lett. 2005 Apr 28;7(9):1707-9. doi: 10.1021/ol0473389.

Authors

Chunling Fu¹, Shengming Ma

Affiliation

¹ Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang, P. R. China.

PMID: 15844886
DOI: 10.1021/ol0473389

Abstract

[reaction: see text] 2(E),4-Alkadienoates were prepared highly stereoselectively via the Pd(0)/Ag(2)CO(3)-cocatalyzed reaction of 3,4-alkadienoates and aryl halides. The reaction is believed to proceed via the oxidative addition-carbopalladation-beta-H elimination process. Compared to the other reported methods for the synthesis of 2,4-alkadienoates, in which usually only disubstituted C=C bonds were formed, the current reaction forms the trisubstituted or even tetrasubstituted C=C bond highly stereoselectively.