Double Strain‐Release (3+3)‐Cycloaddition: Lewis Acid Catalyzed Reaction of Bicyclobutane Carboxylates and Aziridines
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)<sub>3</sub> 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.
Authors
- M. V. George (ORCID: https://orcid.org/0000-0002-8591-5765)
- Daniel Bodo Werz (ORCID: https://orcid.org/0000-0002-3973-2212)
- Daniil A. Knyazev (ORCID: https://orcid.org/0000-0003-1343-6893)
- Jasper Mindner
- Silas Wittmer
Institutions
- University of Freiburg (DE)
Publication Details
- Journal
- Chemistry - A European Journal
- Published
- 2024-12-03
- DOI
- https://doi.org/10.1002/chem.202404099
- Citations
- 15
- Primary Topic
- Synthesis and Catalytic Reactions
- Type
- article
- Field-Weighted Citation Impact
- 3.75
Funders
- Deutscher Akademischer Austauschdienst
- Albert-Ludwigs-Universität Freiburg
- Studienstiftung des Deutschen Volkes