A new tandem synthesis of bis(β,β'-dialkoxy carbonyl) compounds by oxidative cleavage of aziridines under metal-free conditions
An efficient and new approach has been developed to synthesize bis(β,β'-dialkoxy carbonyl) derivatives through the reaction between N-tosylaziridines and malonate esters under ambient air using tBuOK in DMSO solvent. A plausible reaction pathway has been predicted. Control experiments suggested that the reactions proceed through the formation of α-aminoketones. This reaction offers a broad substrate scope, metal-free synthesis, excellent regioselectivity, easily accessible reactants, and simple operation. A gram-scale synthesis demonstrates the potential applications of the present method.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2020 |
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| Erschienen: |
2020 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:18 |
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| Enthalten in: |
Organic & biomolecular chemistry - 18(2020), 3 vom: 22. Jan., Seite 551-556 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Samanta, Satyajit [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Revised 07.02.2020 published: Print Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1039/c9ob02451d |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM304940569 |
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| 100 | 1 | |a Samanta, Satyajit |e verfasserin |4 aut | |
| 245 | 1 | 2 | |a A new tandem synthesis of bis(β,β'-dialkoxy carbonyl) compounds by oxidative cleavage of aziridines under metal-free conditions |
| 264 | 1 | |c 2020 | |
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| 500 | |a Date Revised 07.02.2020 | ||
| 500 | |a published: Print | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a An efficient and new approach has been developed to synthesize bis(β,β'-dialkoxy carbonyl) derivatives through the reaction between N-tosylaziridines and malonate esters under ambient air using tBuOK in DMSO solvent. A plausible reaction pathway has been predicted. Control experiments suggested that the reactions proceed through the formation of α-aminoketones. This reaction offers a broad substrate scope, metal-free synthesis, excellent regioselectivity, easily accessible reactants, and simple operation. A gram-scale synthesis demonstrates the potential applications of the present method | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 700 | 1 | |a Santra, Sougata |e verfasserin |4 aut | |
| 700 | 1 | |a Chatterjee, Rana |e verfasserin |4 aut | |
| 700 | 1 | |a Majee, Adinath |e verfasserin |4 aut | |
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