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

Merabet-Khelassi, Mounia;Aribi-Zouioueche, Louisa;Riant, Olivier
(2017) Research on Chemical Intermediates : an international journal — Vol. 43, n° 10, p. 5293-5303 (2017)

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  • Merabet-Khelassi, MouniaBadji Mokhtar Annaba-University
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  • Aribi-Zouioueche, LouisaBadji Mokhtar Annaba-University
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  • Riant, Olivierorcid-logoUCLouvain
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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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Merabet-Khelassi, M., Aribi-Zouioueche, L., & Riant, O. (2017). Synthesis of 1,2-disubstituted aminoarylferrocene as direct route to enantioenriched 2-hydroxymethyl-1-phenylferrocene via enzymatic kinetic resolution. Research on Chemical Intermediates : an international journal, 43(10), 5293-5303. https://doi.org/10.1007/s11164-017-2926-3 (Original work published 2017)