Ratzenboeck, Andreas and Kobras, Manuel and Rustler, Anna and Reiser, Oliver (2024) Lewis Acid Catalyzed Cyclopropane Ring-Opening-Cyclization Cascade Using Thioureas as a N,N-bisnucleophile: Synthesis of Bicyclic Furo-, Pyrano-, and Pyrrololactams via a Formal [4+1]-Addition. CHEMISTRY-A EUROPEAN JOURNAL, 30 (48). ISSN 0947-6539, 1521-3765
Full text not available from this repository. (Request a copy)Abstract
Fused bicyclic cyclopropanes were converted by Lewis acid-catalysis with thioureas to furo-, pyrano, and pyrrololactams with yields of up to 99 % and high diastereoselectivity. The formation of the title compounds, representing a formal [4+1]-cycloaddition to a donor-acceptor substituted cyclopropane, follows a cascade reaction involving SN1-type ring-opening addition and cyclization. Thiourea, being a cost-effective and odorless reagent, acts as an N,N-bis-nucleophile to generate bicyclic compounds containing an N-substituted gamma-lactam moiety.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | DONOR-ACCEPTOR CYCLOPROPANES; ENANTIOSELECTIVE SYNTHESIS; BOND INSERTION; DERIVATIVES; Cycloaddition; Cyclopropanes; Thiourea; Lewis acids; Furolactam |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 25 Jul 2025 08:44 |
| Last Modified: | 25 Jul 2025 08:44 |
| URI: | https://pred.uni-regensburg.de/id/eprint/63773 |
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