Visible-Light-Activated Catalytic Enantioselective beta-Alkylation of alpha, beta-Unsaturated 2-Acyl Imidazoles Using Hantzsch Esters as Radical Reservoirs

Autor(es)

Huang, Xiaoqiang ^[2]

Afiliação do(s) autor(es)

^[1] Philipps Univ Marburg, Fachbereich Chem, Hans Meerwein Str 4, D-35043 Marburg - Germany

• Tipo de documento: Artigo Científico
• Fonte: Journal of Organic Chemistry; v. 83, n. 18, p. 10922-10932, SEP 21 2018.
• Citações Web of Science: 12

Resumo

An efficient and practical method for the enantioselective beta-functionalization of alpha, beta-unsaturated 2-acyl imidazoles is described. The method uses a previously devised chiral-at-metal rhodium catalyst (Lambda-RhS, 4 mol %) along with Hantzsch ester derivatives as alkyl radical sources. The rhodium complex exerts a dual role as the visible-light-absorbing unit upon substrate binding and as the asymmetric catalyst. The method provides up to quantitative yields with excellent enantioselectivities up to 98% ee and can be classified as a redox-neutral, electron-transfer-catalyzed reaction. (AU)

• Processo FAPESP: 17/06836-4 - Síntese de Di-hidrocumarinas Glicosiladas Através do Uso de Catálise Fotoredox Assimétrica: Obtenção de Potenciais Inibidores da Proteína SGLT2
• Beneficiário: Francisco Fávaro de Assis
• Modalidade de apoio: Bolsas no Exterior - Estágio de Pesquisa - Pós-Doutorado
• Processo FAPESP: 13/07607-8 - CMPO - Centro Multidisciplinar de Pesquisa em Obesidade e Doenças Associadas
• Beneficiário: Licio Augusto Velloso
• Modalidade de apoio: Auxílio à Pesquisa - Centros de Pesquisa, Inovação e Difusão - CEPIDs