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Article Dans Une Revue Chemistry - A European Journal Année : 2024

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

Résumé

A convenient and versatile approach to important 1-azaspirocyclic systems relevant to medicinal chemistry and natural products is reported herein. The main strategy relies on a reductive decarboxylative cyclization of redox-active esters which can be rapidly assembled from abundant cyclic azaacids and tailored acceptor sidechains, with a focus on alkyne acceptors enabling the generation of useful exo-alkene moieties. Diastereoconvergent variants were studied and could be achieved either through remote stereocontrol or conformational restriction in bicyclic carbamate substrates. Two sets of metal-free photocatalytic conditions employing inexpensive eosin Y were disclosed and studied experimentally to highlight key mechanistic divergences.

Domaines

Chimie organique
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Origine : Publication financée par une institution

Dates et versions

hal-04563633 , version 1 (29-04-2024)

Identifiants

Citer

Natalia Kiprova, Marine Desnoyers, Rok Narobe, Arthur Klufts‐edel, Juliane Chaud, et al.. Towards a General Access to 1‐Azaspirocyclic Systems via Photoinduced, Reductive Decarboxylative Radical Cyclizations. Chemistry - A European Journal, 2024, 30 (13), pp.e202303841. ⟨10.1002/chem.202303841⟩. ⟨hal-04563633⟩
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