Double strain‐release (3+3)‐cycloaddition: Lewis acid catalyzed reaction of bicyclobutane carboxylates and aziridines

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Abstract: A (3+3)-cycloaddition to afford 2-azabiyclo[3.1.1]heptanes was realized by reacting highly strained aryl bicyclo[1.1.0]butane (BCBs) carboxylates with tosylated aziridines. Under Sc(OTf)3 catalysis the transformation proceeded smoothly under mild conditions to the corresponding bicyclic products bearing at the bridgeheads of the embedded four-membered ring aryl and ester moieties, respectively. This reaction is a rare example of a cycloaddition of two highly strained ring systems under Lewis acid catalysis. Mechanistic experiments provided insights into the reaction mechanism

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Notes: Chemistry – a European journal. - 31, 9 (2025) , e202404099, ISSN: 1521-3765

Event: Veröffentlichung

(where): Freiburg

(who): Universität

(when): 2024

Creator: George, Malini
Mindner, Jasper
Wittmer, Silas
Knyazev, Daniil A.
Werz, Daniel B.

DOI: 10.1002/chem.202404099

URN: urn:nbn:de:bsz:25-freidok-2608950

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:34 AM CEST

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Associated

George, Malini
Mindner, Jasper
Wittmer, Silas
Knyazev, Daniil A.
Werz, Daniel B.
Universität

Time of origin

2024

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