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

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 transesterifi...

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Bibliographic Details
Published in:Research on Chemical Intermediates
Main Authors: Merabet-Khelassi, Mounia, Aribi-Zouioueche, Louisa, Riant, Olivier
Other Authors: UCL - SST/IMCN/MOST - Molecules, Solids and Reactivity
Format: Article in Journal/Newspaper
Language:English
Published: Springer Nature 2017
Subjects:
Antarc*
Antarctica
Online Access:http://hdl.handle.net/2078.1/202058
https://doi.org/10.1007/s11164-017-2926-3
Description
Summary: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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