Synthetic Communications p. 3975 - 3988 (2004)
Update date:2022-09-26
Topics:
Du Moulinet D'Hardemare, Amaury
Jarjayes, Olivier
Mortini, Florent
We have developed a convenient solvent- and catalyst-free selective Mannich reaction of a variety of para-substituted phenols or catechols with paraformaldehyde and ethyl iminodiacetate. With para-substituted phenols and electron-poor catechol, only the monosubstituted benzyliminodiacetic ester is selectively formed in good yield and no disubstituted product is detected. In contrast, electron rich catechols gave mono- or disubstituted derivatives depending on the stoichiometry of ethyliminodiacetate. Furthermore, the reaction is highly regioselective with catechols, since no para derivatives are formed. In addition, we describe a mild acidic hydrolysis of the ester functions, which avoids the degradation of the benzylamine moiety by the quinone methide pathway. So, pure o-hydroxybenzyliminodiacetic acid ligands are obtained in overall good yields.
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Doi:10.1021/jo00178a032
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