TiCl 4 /Et 3 N-Mediated Condensation of Acetate and Formate Esters: Direct Access to β-Alkoxy- and β-Aryloxyacrylates

A methodology to build (E)-β-alkoxy- and (E)-β-aryloxyacrylate moieties from acetate and formate esters promoted by the TiCl /Et N system is presented. The reaction is compatible with a broad range of structural skeletons and elapses through an unusual condensation pathway. Taking into account the o...

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Veröffentlicht in:Organic letters 2016-12, Vol.18 (24), p.6344-6347
Hauptverfasser: Álvarez-Calero, José María, Jorge, Zacarías D, Massanet, Guillermo M
Format: Artikel
Sprache:eng
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Zusammenfassung:A methodology to build (E)-β-alkoxy- and (E)-β-aryloxyacrylate moieties from acetate and formate esters promoted by the TiCl /Et N system is presented. The reaction is compatible with a broad range of structural skeletons and elapses through an unusual condensation pathway. Taking into account the obtained results, we propose a plausible mechanism involving a bimetallic titanium intermediate for this type of transformation.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b03233