Combining Imine Condensation Chemistry with (3,3) Diaza‐Cope Rearrangement for One‐Step Formation of Hydrolytically Stable Chiral Architectures
Abstract: Dynamic covalent chemistry (DCC) has, in recent years, provided valuable tools to synthesize molecular architectures of increasing complexity. We have also taken advantage of imine DCC chemistry to prepare TPMA‐based supramolecular cages for molecular recognition applications. However, the versatility of this approach has as a major drawback the intrinsic hydrolytic lability of imines, which hampers some applications. We present herein a synthetic strategy that combines the advantages of a thermodynamic‐driven formation of a supramolecular structure using imine chemistry, together with the possibility to synthetize chiral hydrolytically stable structures through a [3,3]‐sigmatropic rearrangement. A preliminary mechanistic analysis of this one‐pot synthesis and the scope of the reaction are also discussed.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Combining Imine Condensation Chemistry with (3,3) Diaza‐Cope Rearrangement for One‐Step Formation of Hydrolytically Stable Chiral Architectures ; day:15 ; month:06 ; year:2023 ; extent:6
Angewandte Chemie ; (15.06.2023) (gesamt 6)
- Creator
- DOI
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10.1002/ange.202304490
- URN
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urn:nbn:de:101:1-2023061615024912101042
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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14.08.2025, 11:01 AM CEST
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Associated
- Begato, Federico
- Penasa, Roberto
- Wurst, Klaus
- Licini, Giulia
- Zonta, Cristiano
Other Objects (12)
Combining Imine Condensation Chemistry with (3,3) Diaza‐Cope Rearrangement for One‐Step Formation of Hydrolytically Stable Chiral Architectures
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Reaktionsübergangszustände der Cope- und Diaza-Cope-Umlagerung
Homologation of the Fischer Indolization: A Quinoline Synthesis via Homo‐Diaza‐Cope Rearrangement
Die Diaza-Cope-Umlagerung : Mechanismus und synthetische Anwendung.
Synthesis of Homoallylic Amines via 2-Aza-Cope Rearrangement
Synthesen substituierter Diaza[10]- [Diaza-] und Diaza[14]annulene [Diazaannulene]
Synthesen pyrimidinhomologer, methanoüberbrückter Diaza[10]- [Diaza-] und Diaza[14]annulene [Diazaannulene]
Eludicating Heavy‐Atom‐Tunneling Kinetics in the Cope Rearrangement of Semibullvalene
Synthese elongierter Diaza-π-Donor-Cavitäten [Diaza-pi-Donor-Cavitäten]
Synergistic catalysis for cascade allylation and 2-aza-cope rearrangement of azomethine ylides
Synthesis of icariin from kaempferol through regioselective methylation and para-Claisen–Cope rearrangement
Combining Imine Condensation Chemistry with (3,3) Diaza‐Cope Rearrangement for One‐Step Formation of Hydrolytically Stable Chiral Architectures
Dendritische Diaza-Cope-Umlagerung
Reaktionsübergangszustände der Cope- und Diaza-Cope-Umlagerung
Homologation of the Fischer Indolization: A Quinoline Synthesis via Homo‐Diaza‐Cope Rearrangement
Die Diaza-Cope-Umlagerung : Mechanismus und synthetische Anwendung.
Synthesis of Homoallylic Amines via 2-Aza-Cope Rearrangement
Synthesen substituierter Diaza[10]- [Diaza-] und Diaza[14]annulene [Diazaannulene]
Synthesen pyrimidinhomologer, methanoüberbrückter Diaza[10]- [Diaza-] und Diaza[14]annulene [Diazaannulene]
Eludicating Heavy‐Atom‐Tunneling Kinetics in the Cope Rearrangement of Semibullvalene
Synthese elongierter Diaza-π-Donor-Cavitäten [Diaza-pi-Donor-Cavitäten]
Synergistic catalysis for cascade allylation and 2-aza-cope rearrangement of azomethine ylides
Synthesis of icariin from kaempferol through regioselective methylation and para-Claisen–Cope rearrangement
Combining Imine Condensation Chemistry with (3,3) Diaza‐Cope Rearrangement for One‐Step Formation of Hydrolytically Stable Chiral Architectures
Dendritische Diaza-Cope-Umlagerung
Reaktionsübergangszustände der Cope- und Diaza-Cope-Umlagerung
Homologation of the Fischer Indolization: A Quinoline Synthesis via Homo‐Diaza‐Cope Rearrangement
Die Diaza-Cope-Umlagerung : Mechanismus und synthetische Anwendung.
Synthesis of Homoallylic Amines via 2-Aza-Cope Rearrangement
Synthesen substituierter Diaza[10]- [Diaza-] und Diaza[14]annulene [Diazaannulene]
Synthesen pyrimidinhomologer, methanoüberbrückter Diaza[10]- [Diaza-] und Diaza[14]annulene [Diazaannulene]
Eludicating Heavy‐Atom‐Tunneling Kinetics in the Cope Rearrangement of Semibullvalene
Synthese elongierter Diaza-π-Donor-Cavitäten [Diaza-pi-Donor-Cavitäten]
Synergistic catalysis for cascade allylation and 2-aza-cope rearrangement of azomethine ylides