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...
Published in: | Research on Chemical Intermediates |
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Main Authors: | , , |
Other Authors: | |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
Springer Nature
2017
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Subjects: | |
Online Access: | http://hdl.handle.net/2078.1/202058 https://doi.org/10.1007/s11164-017-2926-3 |
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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