Enantioselective Copper-Catalyzed Synthesis of Trifluoromethyl-Cyclopropylboronates

A copper-catalyzed enantioselective cyclopropanation involving trifluorodiazoethane in the presence of alkenyl boronates has been developed. This transformation enables the preparation of 2-substituted-3-(trifluoromethyl)cyclopropylboronates with high levels of stereocontrol. The products are valuab...

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Detalhes bibliográficos
Autores: Altarejos Salido, Julia|||0000-0002-2871-8597; Sucunza Sáenz, David|||0000-0002-3307-4204; Vaquero López, Juan José|||0000-0002-3820-9673; Carreras Pérez Aradros, Javier|||0000-0002-1521-6758
Tipo de documento: Artigo
Data de publicação:2021
País:España
Recursos:Universidad de Alcalá (UAH)
Repositório:e_Buah Biblioteca Digital Universidad de Alcalá
Idioma:Inglês
OAI Identifier:oai:ebuah.uah.es:10017/49328
Acesso em linha:http://hdl.handle.net/10017/49328
https://dx.doi.org/10.1021/acs.orglett.1c02420
Nível de acesso:Acesso aberto
Palavra-chave:(Trifluoromethyl)cyclopropylboronates
Enantioselective cyclopropanation
Trifluorodiazoethane
Alkenyl boronates
Copper catalysis
Trifluoromethylcyclopropanes
Química
Chemistry
Descrição
Resumo:A copper-catalyzed enantioselective cyclopropanation involving trifluorodiazoethane in the presence of alkenyl boronates has been developed. This transformation enables the preparation of 2-substituted-3-(trifluoromethyl)cyclopropylboronates with high levels of stereocontrol. The products are valuable synthetic intermediates by transformation of the boronate group. This methodology can be applied to the synthesis of novel trifluoromethylated analogues of trans-2-arylcyclopropylamines, which are prevalent motifs in biologically active compounds.