TiCl4/Et3N-Mediated Condensation of Acetate and Formate Esters: Direct Access to β-Alkoxy- and β-Aryloxyacrylates | Zendy

José María Álvarez | Zendy; Zacarı́as D. Jorge | Zendy; Guillermo M. Massanet | Zendy

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TiCl₄/Et₃N-Mediated Condensation of Acetate and Formate Esters: Direct Access to β-Alkoxy- and β-Aryloxyacrylates

Author(s) -

José María Álvarez,

Zacarı́as D. Jorge,

Guillermo M. Massanet

Publication year - 2016

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.6b03233

Subject(s) - chemistry , alkoxy group , formate , bimetallic strip , condensation , condensation reaction , titanium , methyl formate , transformation (genetics) , medicinal chemistry , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , biochemistry , gene , alkyl , physics , thermodynamics

A methodology to build (E)-β-alkoxy- and (E)-β-aryloxyacrylate moieties from acetate and formate esters promoted by the TiCl 4 /E 3 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.

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