Enantioselective Synthesis of Complex Fused Heterocycles through Chiral Phosphoric Acid Catalyzed Intramolecular Inverse-Electron-Demand Aza-Diels-Alder Reactions
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim..
A stable asymmetric intramolecular Povarov reaction has been established to provide an efficient method to access structurally diverse trans,trans-trisubstituted tetrahydrochromeno[4,3-b]quinolines in high stereoselectivities of up to >99:1 diastereomeric ratio and 99 % enantiomeric excess, without any purification step. Additionally, to facilitate large-scale application of this method, a low catalyst loading protocol was employed, 0.2 mol % chiral phosphoric acid, which provided the cycloadducts without any loss in yield and enantioselectivity. Theoretical studies revealed that the reaction occurred through a sequential Mannich reaction and an intramolecular Friedel-Crafts reaction, wherein the phosphoric acid acted as a bifunctional catalyst to activate the para-phenolic dienophile and N-2-hydroxy-2-azadiene simultaneously.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2020 |
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| Erschienen: |
2020 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:26 |
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| Enthalten in: |
Chemistry (Weinheim an der Bergstrasse, Germany) - 26(2020), 6 vom: 27. Jan., Seite 1406-1413 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Jarrige, Lucie [VerfasserIn] |
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| Links: |
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| Themen: |
Chirality |
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| Anmerkungen: |
Date Completed 03.02.2020 Date Revised 03.02.2020 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1002/chem.201904902 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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NLM302677925 |
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| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. | ||
| 520 | |a A stable asymmetric intramolecular Povarov reaction has been established to provide an efficient method to access structurally diverse trans,trans-trisubstituted tetrahydrochromeno[4,3-b]quinolines in high stereoselectivities of up to >99:1 diastereomeric ratio and 99 % enantiomeric excess, without any purification step. Additionally, to facilitate large-scale application of this method, a low catalyst loading protocol was employed, 0.2 mol % chiral phosphoric acid, which provided the cycloadducts without any loss in yield and enantioselectivity. Theoretical studies revealed that the reaction occurred through a sequential Mannich reaction and an intramolecular Friedel-Crafts reaction, wherein the phosphoric acid acted as a bifunctional catalyst to activate the para-phenolic dienophile and N-2-hydroxy-2-azadiene simultaneously | ||
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| 650 | 4 | |a hydrogen bonds | |
| 650 | 4 | |a phosphoric acids | |
| 700 | 1 | |a Gandon, Vincent |e verfasserin |4 aut | |
| 700 | 1 | |a Masson, Géraldine |e verfasserin |4 aut | |
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