What question did this study set out to answer?

The study aims to develop a new method for synthesizing medium-sized cyclic aminals using copper catalysis.

February 22, 2026Organic Letters0 citations

Copper-Catalyzed Synthesis of Medium-Sized Cyclic Aminals via Annulation of Ketenimines and N -Acyliminium Ions

CCChinmayee Choudhury SBSubhamoy BiswasIndian Institute of Technology Guwahati BPBikoshita PorasharIndian Institute of Technology Guwahati

Key Points

The study aims to develop a new method for synthesizing medium-sized cyclic aminals using copper catalysis.
Developed a CuBr-catalyzed cascade strategy for synthesis.
Generated ketenimines in situ via a click reaction.
Facilitated cyclization of ketenimines with n-acyliminium ions.
Explored broad substrate compatibility and scalability.
Successfully synthesized a variety of polycyclic aminals.
Achieved frameworks ranging from 6- to 10-membered rings.
Demonstrated the versatility of the synthetic approach.

Abstract

A CuBr-catalyzed intermolecular cascade strategy was developed to access medium-sized polycyclic aminals. While conventional cyclization encounters severe limitations due to inherent enthalpic and entropic constraints, this approach overcomes such challenges through in situ generation of ketenimines via a Cu-catalyzed click reaction, followed by their cyclization with N-acyliminium ions. The protocol features broad substrate compatibility, scalability, and versatility. Notably, a wide range of polycyclic aminals, from 6- to 10-membered frameworks, can be achieved using this strategy.

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