An intramolecular Heck reaction of enol ethers involving β-alkoxyl elimination followed by the β-hydride elimination process: access to (Z)-ortho-formyl/keto-cinnamates

Manman Sun; Haibo Wu; Haijian Wu; Zhiming Wang

doi:10.1039/c9cc08133j

An intramolecular Heck reaction of enol ethers involving β-alkoxyl elimination followed by the β-hydride elimination process: access to (Z)-ortho-formyl/keto-cinnamates

Chem Commun (Camb). 2019 Nov 28;55(96):14422-14425. doi: 10.1039/c9cc08133j.

Authors

Manman Sun¹, Haibo Wu, Haijian Wu, Zhiming Wang

Affiliation

¹ Advanced Research Institute and Department of Chemistry, Taizhou University, 1139 Shifu Avenue, Taizhou 318000, P. R. China. zhiming@tzc.edu.cn wzmmol@hotmail.com.

PMID: 31720626
DOI: 10.1039/c9cc08133j

Abstract

A highly regio- and stereoselective intramolecular Heck reaction of enol ethers involving β-alkoxyl elimination followed by the β-hydride elimination process has been developed. Various o-iodobenzyl enol ethers derived from allenoates or alkynoates are found to be efficient substrates for the syntheses of (Z)-ortho-formyl/keto-cinnamates. It is the first attempt to realize the β-alkoxy elimination of enol ethers in a palladium-catalyzed Heck reaction.