Méndez-Sánchez, D;
Lavandera, I;
Gotor, V;
Gotor-Fernández, V;
(2017)
Novel chemoenzymatic oxidation of amines into oximes based on hydrolase-catalysed peracid formation.
Organic & Biomolecular Chemistry
, 15
(15)
pp. 3196-3201.
10.1039/c7ob00374a.
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Abstract
The efficient transformation of benzylamines into the corresponding oximes has been described by means of a chemoenzymatic process. This strategy is based on a two-step sequence developed in one-pot at 30 °C and atmospheric pressure. First, the formation of a reactive peracid intermediate occurs by means of a lipase-catalysed perhydrolysis reaction, and then this peracid acts as a chemical oxidising agent of the amines. A total of nine ketoximes were isolated in high purity after a simple extraction protocol (90–98% isolated yield), while for the eleven synthesised aldoximes a further column chromatography purification was required (71–82% isolated yield). In all cases excellent selectivities were attained, offering a practical method for amine oxidation in short reaction times (1 hour). The environmental impact of the process was analysed and compared with a recently published alternative chemical synthesis, finding for this metric a good E-factor value.
| Type: | Article |
|---|---|
| Title: | Novel chemoenzymatic oxidation of amines into oximes based on hydrolase-catalysed peracid formation |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1039/c7ob00374a |
| Publisher version: | https://doi.org/10.1039/c7ob00374a |
| Language: | English |
| Additional information: | This version is the author accepted manuscript. For information on re-use, please refer to the publisher’s terms and conditions. |
| UCL classification: | UCL UCL > Provost and Vice Provost Offices > UCL BEAMS UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry |
| URI: | https://discovery.ucl.ac.uk/id/eprint/10071576 |
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