Towards a General Access to 1-Azaspirocyclic Systems via Photoinduced, Reductive Decarboxylative Radical Cyclizations

Kiprova, Natalia and Desnoyers, Marine and Narobe, Rok and Klufts-Edel, Arthur and Chaud, Juliane and Koenig, Burkhard and Compain, Philippe and Kern, Nicolas (2024) Towards a General Access to 1-Azaspirocyclic Systems via Photoinduced, Reductive Decarboxylative Radical Cyclizations. CHEMISTRY-A EUROPEAN JOURNAL, 30 (13). e202303841. ISSN 0947-6539, 1521-3765

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Abstract

A simple yet versatile strategy for the construction of important 1-azaspirocyclic scaffolds is described. Alkynyl-tethered N-hydroxyphthalimide esters, swiftly assembled through an alkylation/deprotection/activation sequence, undergo photoinduced reductive decarboxylative radical 5-exo and 6-exo-dig cyclizations employing eosin Y (EY) as inexpensive photocatalyst. The key step can proceed in a diastereoconvergent manner and affords diverse ring systems relevant to medicinal chemistry and natural products.+image

Item Type: Article
Uncontrolled Keywords: BOND-DISSOCIATION ENERGIES; ELECTRON-TRANSFER; METAL-FREE; RING-CLOSURE; EOSIN Y; VINYL; CONSTRUCTION; RULES; N-(ACYLOXY)PHTHALIMIDES; STEREOCHEMISTRY; azaspirocycles; radicals; alkynes; decarboxylation; photoredox
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König
Depositing User: Dr. Gernot Deinzer
Date Deposited: 14 Jan 2026 05:52
Last Modified: 14 Jan 2026 05:52
URI: https://pred.uni-regensburg.de/id/eprint/64373

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