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.
- 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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Donor‐Acceptor Aminocyclobutane Monoesters: Synthesis and Silylium‐Catalyzed (4+2) Annulation with Indoles ; day:12 ; month:05 ; year:2023 ; extent:9
Angewandte Chemie ; (12.05.2023) (gesamt 9)
- Creator
- DOI
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10.1002/ange.202302420
- URN
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urn:nbn:de:101:1-2023051315124975210964
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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14.08.2025, 10:48 AM CEST
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Associated
- Robert, Emma G. L.
- Pirenne, Vincent
- Wodrich, Matthew
- Waser, Jérôme
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Donor-acceptor cyclopropanes in organic synthesis
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Ni-Catalyzed Annulation of Donor–Acceptor Oxiranes with Imines
Halogenated Donor–Acceptor Cyclopropanes as Donor–Acceptor Cyclopropene Surrogates
Halogenated Donor–Acceptor Cyclopropanes as Donor–Acceptor Cyclopropene Surrogates
(4+3) Annulation of Donor‐Acceptor Cyclopropanes and Azadienes: Highly Stereoselective Synthesis of Azepanones
(4+3) Annulation of Donor‐Acceptor Cyclopropanes and Azadienes: Highly Stereoselective Synthesis of Azepanones
Selective C−H Bond Functionalization of Unprotected Indoles by Donor‐Acceptor Carbene Insertion
Organic Donor‐Acceptor Systems for Photocatalysis
Donor-acceptor cyclopropanes in organic synthesis
Donor‐Acceptor Activation of Carbon Dioxide
A mechanochromic donor-acceptor torsional spring