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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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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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Publication details

The article was received on 16 Oct 2019, accepted on 04 Nov 2019 and first published on 06 Nov 2019


Article type: Communication
DOI: 10.1039/C9CC08133J
Chem. Commun., 2019, Advance Article

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    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

    M. Sun, H. Wu, H. Wu and Z. Wang, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C9CC08133J

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