Work

Double Strain‐Release (3+3)‐Cycloaddition: Lewis Acid Catalyzed Reaction of Bicyclobutane Carboxylates and Aziridines

Year: 2024

Type: article

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.

Source: Chemistry - A European Journal

DOI: 10.1002/chem.202404099

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

Institution: University of Freiburg

Language: English

Topic: Organic Chemistry Cycloaddition Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,640

Funders: Fonds der Chemischen Industrie, Deutscher Akademischer Austauschdienst, Albert-Ludwigs-Universität Freiburg, Studienstiftung des Deutschen Volkes