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- Title
Synthesis of Functionalized Cyclopentene Derivatives from Vinyldiazo Compounds and Vinylazides through Sequential Copper-Promoted [3+2] Cycloaddition/Azide Rearrangement.
- Authors
López, Enol; López, Luis A.
- Abstract
The reaction of vinylazides with alkenyldiazo compounds in the presence of [Cu(CH3CN)4][BF4] provided cyclopentene derivatives with retention of the azide functionality. This process likely involves a sequence comprising: 1) decomposition of the diazo component with generation of a copper alkenylcarbene species; 2) stepwise regioselective [3+2] cycloaddition; 3) allylic azide rearrangement. This method is compatible with a broad range of substrates. We also show that the azide-containing cycloadducts can be efficiently converted into the corresponding amine and triazole derivatives.
- Subjects
CYCLOPENTENE derivatives; CYCLOPENTENES synthesis; ALKENYL group; CARBENE analogues; FUNCTIONAL groups; HETEROCYCLIC compounds
- Publication
Angewandte Chemie, 2017, Vol 129, Issue 18, p5203
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201701572