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
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 o...
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ftmdpi:oai:mdpi.com:/2073-4344/13/4/703/ 2023-08-20T04:02:25+02:00 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 Julio Romero-Ibañez Marina A. Ortega-Rojas Jonathan R. Valdéz-Camacho Luis G. Hernández-Vázquez Fernando Sartillo-Piscil Jaime Escalante 2023-04-06 application/pdf https://doi.org/10.3390/catal13040703 EN eng Multidisciplinary Digital Publishing Institute Computational Catalysis https://dx.doi.org/10.3390/catal13040703 https://creativecommons.org/licenses/by/4.0/ Catalysts; Volume 13; Issue 4; Pages: 703 trans -3-Alkoxyamino-4-oxygenated-2-piperidones selective C−H oxidation transition-metal-free enzymatic resolution CAL-B deconstructive lactamization alkaloids Text 2023 ftmdpi https://doi.org/10.3390/catal13040703 2023-08-01T09:35:03Z 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. Text Antarc* Antarctica MDPI Open Access Publishing Catalysts 13 4 703 |
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Open Polar |
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MDPI Open Access Publishing |
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ftmdpi |
language |
English |
topic |
trans -3-Alkoxyamino-4-oxygenated-2-piperidones selective C−H oxidation transition-metal-free enzymatic resolution CAL-B deconstructive lactamization alkaloids |
spellingShingle |
trans -3-Alkoxyamino-4-oxygenated-2-piperidones selective C−H oxidation transition-metal-free enzymatic resolution CAL-B deconstructive lactamization alkaloids Julio Romero-Ibañez Marina A. Ortega-Rojas Jonathan R. Valdéz-Camacho Luis G. Hernández-Vázquez Fernando Sartillo-Piscil Jaime Escalante 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 |
topic_facet |
trans -3-Alkoxyamino-4-oxygenated-2-piperidones selective C−H oxidation transition-metal-free enzymatic resolution CAL-B deconstructive lactamization alkaloids |
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. |
format |
Text |
author |
Julio Romero-Ibañez Marina A. Ortega-Rojas Jonathan R. Valdéz-Camacho Luis G. Hernández-Vázquez Fernando Sartillo-Piscil Jaime Escalante |
author_facet |
Julio Romero-Ibañez Marina A. Ortega-Rojas Jonathan R. Valdéz-Camacho Luis G. Hernández-Vázquez Fernando Sartillo-Piscil Jaime Escalante |
author_sort |
Julio Romero-Ibañez |
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 |
title_short |
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 |
title_full |
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 |
title_fullStr |
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 |
title_full_unstemmed |
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 |
title_sort |
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 |
publisher |
Multidisciplinary Digital Publishing Institute |
publishDate |
2023 |
url |
https://doi.org/10.3390/catal13040703 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Catalysts; Volume 13; Issue 4; Pages: 703 |
op_relation |
Computational Catalysis https://dx.doi.org/10.3390/catal13040703 |
op_rights |
https://creativecommons.org/licenses/by/4.0/ |
op_doi |
https://doi.org/10.3390/catal13040703 |
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Catalysts |
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13 |
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4 |
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703 |
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1774712846628683776 |