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Updated: Jun 5, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Organocatalytic Hat Trick: 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD)-Catalyzed Synthesis of Cyclic Imides via an
Chunling Blue Lan1, Karine Auclair1
1Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 0B8, Canada.
Abstract:
1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD) was used for the synthesis of cyclic imides via an amidation-cyclization-elimination cascade. This organocatalytic transformation features both the traditional reactivity of TBD and its unprecedented C-C bond cleavage capability, allowing rapid and efficient access to cyclic imides. This method is compatible with the late-stage functionalization of complex molecules and the synthesis of bioactive molecules. Both experimental and computational approaches were employed to gain a better understanding of the reaction mechanism.
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