An Approach to the Synthesis of a Hepatitis C Virus Inhibitor through a Proline-Catalyzed 1,3-Dipolar Cycloaddition Using Acrolein

An efficient and easy protocol for performing 1,3-dipolar cycloaddition using azomethine ylides and acrolein is presented. The reaction catalyzed by d-proline allows the synthesis of C-3 unsubstituted pyrrolidines. The application of this methodology to the synthesis of an advanced intermediate in t...

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Detalhes bibliográficos
Autores: Ugarriza Serrano, Iratxe, Reyes Martín, Efraim, Prieto Aretxabaleta, Liher, Uria Pujana, Uxue, Carrillo Fernández, María Luisa, Vicario Hernando, José Luis
Formato: artículo
Fecha de publicación:2021
País:España
Recursos:Universidad del País Vasco
Repositorio:Addi. Archivo Digital para la Docencia y la Investigación
OAI Identifier:oai:addi.ehu.eus:10810/63394
Acesso em linha:http://hdl.handle.net/10810/63394
Access Level:acceso abierto
Palavra-chave:prolinol
cycloaddition
dipole
pyrrolidine
aminomalonate
acrolein
ylides
Descrição
Resumo:An efficient and easy protocol for performing 1,3-dipolar cycloaddition using azomethine ylides and acrolein is presented. The reaction catalyzed by d-proline allows the synthesis of C-3 unsubstituted pyrrolidines. The application of this methodology to the synthesis of an advanced intermediate in the preparation of a Hepatitis C virus inhibitor is presented. Final attempts to complete the synthesis of the target inhibitor results in the preparation of its C-4 epimer in good overall yield