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Organocatalytic Hat Trick: 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD)-Catalyzed Synthesis of Cyclic Imides via an Amidation–Cyclization–Elimination Cascade

2024/12/12 by Chunling Blue Lan, Karine Auclair · 1 voice
Biochemistry, Genetics and Molecular Biology · Chemistry · #Asymmetric Hydrogenation and Catalysis #Chemical Synthesis and Analysis #Cyclopropane Reaction Mechanisms

paper · doi:10.1021/acs.joc.4c02649

openalex publication_date 2024/12/12 · openalex created_date 2025/10/10 · openalex updated_date 2026/06/18

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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