Electrochemical Formal (3 + 2) Cycloaddition/Imidation Cascade: Easy Access to Triazabicyclo-[3.3.0] Scaffolds

The established strategy unveils an electrochemical formal (3 + 2) cycloaddition/imidation sequence between <i>N</i>-aryl glycinamides and 5-methoxyoxazoles, furnishing diversely substituted imidazoline fused pyrrole-2,5-dione scaffolds. This diastereocontrolled cascade annulation operates with the assistance of ZnCl<sub>2</sub> as a Lewis acid catalyst and provides two contiguous stereocenters as part of the [3.3.0]triazabicyclic core structure. An extensive range of distinct functionalities is well tolerated under this mild electrochemical condition, contributing to a broad substrate scope.

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Publication Details

Journal
Organic Letters
Published
2025-09-19
DOI
https://doi.org/10.1021/acs.orglett.5c03582
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.00
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article

Electrochemical Formal (3 + 2) Cycloaddition/Imidation Cascade: Easy Access to Triazabicyclo-[3.3.0] Scaffolds

Suman De Sarkar, Samrat Mallick, Pooja Bhardwaj, Dipankar Das
Organic Letters
Radical Photochemical Reactions
article

Electrochemical Formal (3 + 2) Cycloaddition/Imidation Cascade: Easy Access to Triazabicyclo-[3.3.0] Scaffolds

Suman De Sarkar, Samrat Mallick, Pooja Bhardwaj, Dipankar Das
article en

Abstract

The established strategy unveils an electrochemical formal (3 + 2) cycloaddition/imidation sequence between <i>N</i>-aryl glycinamides and 5-methoxyoxazoles, furnishing diversely substituted imidazoline fused pyrrole-2,5-dione scaffolds. This diastereocontrolled cascade annulation operates with the assistance of ZnCl<sub>2</sub> as a Lewis acid catalyst and provides two contiguous stereocenters as part of the [3.3.0]triazabicyclic core structure. An extensive range of distinct functionalities is well tolerated under this mild electrochemical condition, contributing to a broad substrate scope.

Organic LettersVol. 27(39)
Indian Institute of Science Education and Research Kolkata (IN)
Openalex Percentile: Top 81%
Radical Photochemical Reactions
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