Cycloaddition of bicyclo[1.1.0]butanes with enamides for the efficient synthesis of 2-amino-bicyclo[2.1.1]hexanes

Abstract

Here, we develop a mild and scalable approach for the synthesis of 2-amino-bicyclo[2.1.1]hexanes via Lewis acid-catalyzed (3+2) cycloaddition of bicyclo[1.1.0]butanes (BCBs) with enamides. The practicality of this methodology has been demonstrated by scale-up reactions and product modifications, providing highly valuable aniline bioisosteres and structurally complex three-dimensional cyclic amines.

Graphical abstract: Cycloaddition of bicyclo[1.1.0]butanes with enamides for the efficient synthesis of 2-amino-bicyclo[2.1.1]hexanes

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Article information

Article type
Communication
Submitted
22 May 2025
Accepted
23 Jun 2025
First published
25 Jun 2025

Chem. Commun., 2025, Advance Article

Cycloaddition of bicyclo[1.1.0]butanes with enamides for the efficient synthesis of 2-amino-bicyclo[2.1.1]hexanes

Y. Zhu, S. Yang, H. Chen, F. Zhang, E. Pu, P. Jiang, Y. Jin, H. Zhang and J. Chen, Chem. Commun., 2025, Advance Article , DOI: 10.1039/D5CC02908B

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