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?

Chemical Communications Pub Date: 2019-11-06 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.

Graphical abstract: 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
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