| dc.creator | MARINA ARGELIA ORTEGA ROJAS | |
| dc.creator | JONATHAN ROMAN VALDEZ CAMACHO | |
| dc.creator | Jaime Escalante García | |
| dc.date | 2023-04-06 | |
| dc.date.accessioned | 2023-07-25T12:48:35Z | |
| dc.date.available | 2023-07-25T12:48:35Z | |
| dc.identifier | 2073-4344 | |
| dc.identifier | http://riaa.uaem.mx/handle/20.500.12055/3588 | |
| dc.identifier.uri | https://repositorioslatinoamericanos.uchile.cl/handle/2250/7792893 | |
| dc.description | A general chemo-enzymatic approach to synthesize both enantioenriched trans-3-alkoxyamino-4-oxy-2-piperidones, which are important scaffold for various naturally occurring alkaloids, is
reported. To this end, a selective transition-metal-free dual C−H oxidation of piperidines mediated
by the TEMPO oxoammonium cation (TEMPO+) was used, followed by enzymatic resolution of the
corresponding alkoxyamino-2-piperidones with Candida antarctica lipase (CAL-B), to yield the title
compounds in high enantiomeric excess (ee). The absolute configuration of both enantioenriched
compounds was determined using chemical correlation and circular dichroism (CD) spectroscopy.
The former method highlights the oxidative ring contraction of the trans-alkoxyamine-2-piperidone
ring into its corresponding 2-pyrrolidinone. | |
| dc.format | pdf | |
| dc.language | eng | |
| dc.publisher | MDPI Open Access Journals | |
| dc.relation | Catalysts | |
| dc.relation | 4 | |
| dc.relation | 13 | |
| dc.relation | https://www.mdpi.com/2073-4344/13/4/703 | |
| dc.relation | info:eu-repo/semantics/altIdentifier/issn/2073-4344 | |
| dc.rights | info:eu-repo/semantics/openAccess | |
| dc.rights | http://creativecommons.org/licenses/by/4.0 | |
| dc.subject | info:eu-repo/classification/cti/2 | |
| dc.subject | info:eu-repo/classification/cti/23 | |
| dc.subject | trans-3-Alkoxyamino-4-oxygenated-2-piperidones, selective C−H oxidation, transition-metal-free, enzymatic resolution; CAL-B, deconstructive lactamization | |
| dc.title | Asymmetric Synthesis of trans-3-Alkoxyamino-4-Oxygenated-2-Piperidones Mediated by Transition-Metal-Free Dual C-H Oxidation and Its CAL-B-Assisted Enzymatic Resolution | |
| dc.type | info:eu-repo/semantics/article | |
| dc.coverage | MEX | |
| dc.audience | researchers | |
| dc.audience | students | |
