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Synthesis of 1,2-disubstituted aminoarylferrocene as direct route to enantioenriched 2-hydroxymethyl-1-phenylferrocene via enzymatic kinetic resolution

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Abstract

We describe an easy pathway for synthesis of some 2-substituted aminoarylferrocenes with planar chirality using Negishi cross-coupling as the key step. After derivatization into the arylated ferrocenyl alcohols, kinetic resolution of the racemic 2-hydroxymethyl phenylferrocene (4a) via transesterification was performed using Candida antarctica lipase fraction B immobilized on acrylic resin (CAL-B). For the first time, acetoxymethyl-1-phenylferrocene (3a), resulting acetate, was obtained in enantiomeric excess (ee) up to 99%. To explain the behavior of CAL-B toward this organometallic structure, we compared with the enzymatic acylation of an analogous compound, racemic 2-hydroxymethyl phenylthioferrocene (7).

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Acknowledgements

Algerian Ministry of Education and Scientific Research (FNR 2000 and PNR), Université Catholique de Louvain, and FNRS are gratefully acknowledged for financial support of this work. UCL is acknowledged for a “cooperation au développement” grant.

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Authors and Affiliations

  1. Ecocompatible Asymmetric Catalysis Laboratory (LCAE), Badji Mokhtar Annaba-University, B.P. 12, 23000, Annaba, Algeria

    Mounia Merabet-Khelassi & Louisa Aribi-Zouioueche

  2. Institute of Condensed Matter and Nanosciences Molecules, Solids and Reactivity (IMCN/MOST), Université Catholique de Louvain, Bâtiment Lavoisier, Pl. Louis Pasteur, 1, bte 3, 1348, Louvain La Neuve, Belgium

    Olivier Riant

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  1. Mounia Merabet-Khelassi
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  2. Louisa Aribi-Zouioueche
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  3. Olivier Riant
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Correspondence to Mounia Merabet-Khelassi.

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Merabet-Khelassi, M., Aribi-Zouioueche, L. & Riant, O. Synthesis of 1,2-disubstituted aminoarylferrocene as direct route to enantioenriched 2-hydroxymethyl-1-phenylferrocene via enzymatic kinetic resolution. Res Chem Intermed 43, 5293–5303 (2017). https://doi.org/10.1007/s11164-017-2926-3

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