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Updated: Jun 10, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Catalytic Asymmetric Synthesis of Bicyclic Isothioureas from a Common Enolizable Template
Leire Villaescusa1, Laura Azcune1, Aitor Landa1
1Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, Manuel Lardizabal Pasealekua 3, Donostia-San Sebastian 20018, Spain.
Abstract:
While bicyclic isothiourea (ITU) moieties are found in biologically active molecules and organocatalysts, a catalytic asymmetric synthesis of ITUs is pending. Here, we report the catalytic, enantioselective functionalization of enolizable template II with a variety of electrophiles, including unsaturated ketones, esters, sulfones, nitro compounds, and thiolating reagents, as an entry to enantioenriched bicyclic ITUs III. Scope and limitations are shown, as well as examples of product derivatization.
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