Donor‐Acceptor Aminocyclobutane Monoesters: Synthesis and Silylium‐Catalyzed (4+2) Annulation with Indoles
Abstract: A convenient one‐step synthesis of β‐aminocyclobutane monoesters starting from commercially available reagents is reported. The obtained strained rings undergo (4+2) dearomative annulation with indole partners using silylium catalysis. This organocatalyzed annulation provided tricyclic indolines with four new stereocenters in up to quantitative yield and >95: 5 diastereoselectivity and can proceed both intra‐ and intermolecularly. When performed intramolecularly, the tetracyclic structure of either akuamma or malagasy alkaloids was obtained selectively depending on the temperature of the reaction. This divergent outcome could be rationalized based on DFT calculations.
- Standort
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Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
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Online-Ressource
- Sprache
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Englisch
- Erschienen in
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Donor‐Acceptor Aminocyclobutane Monoesters: Synthesis and Silylium‐Catalyzed (4+2) Annulation with Indoles ; day:12 ; month:05 ; year:2023 ; extent:9
Angewandte Chemie / International edition. International edition ; (12.05.2023) (gesamt 9)
- Urheber
- DOI
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10.1002/anie.202302420
- URN
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urn:nbn:de:101:1-2023051315050863668014
- Rechteinformation
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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14.08.2025, 10:44 MESZ
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Beteiligte
- Robert, Emma G. L.
- Pirenne, Vincent
- Wodrich, Matthew
- Waser, Jérôme
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