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Novel chemoenzymatic oxidation of amines into oximes based on hydrolase-catalysed peracid formation.
| Content Provider | Semantic Scholar |
|---|---|
| Author | Sánchez, Daniel Méndez‐ Lavandera, Iván Gotor, Vicente Gotor-Fernández, Vicente |
| Copyright Year | 2017 |
| 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. |
| Starting Page | 3196 |
| Ending Page | 3201 |
| Page Count | 6 |
| File Format | PDF HTM / HTML |
| DOI | 10.1039/c7ob00374a |
| Alternate Webpage(s) | http://www.rsc.org/suppdata/c7/ob/c7ob00374a/c7ob00374a2.pdf |
| Alternate Webpage(s) | http://discovery.ucl.ac.uk/10071576/1/M%C3%A9ndez-S%C3%A1nchez_Org.%20Biomol.%20Chem.%202017153196-3201%20(postprint).pdf |
| PubMed reference number | 28362446 |
| Alternate Webpage(s) | https://doi.org/10.1039/c7ob00374a |
| Journal | Medline |
| Volume Number | 15 |
| Issue Number | 15 |
| Journal | Organic & biomolecular chemistry |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
