A Straightforward Sequential Approach for the Enantioselective Synthesis of Optically Active alpha-Arylmethanol-1,2,3-Triazoles

Autor(es)

Andrade, Floyd C. D. ^[1] ; Pugnal, Lucas V. B. L. ^[1] ; Betim, Hugo L. I. ^[1] ; Vani, Jessica F. ^[1] ; Zukerman-Schpector, Julio ^[2] ; Schwab, Ricardo S. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Fed Sao Carlos UFSCar, Dept Quim, Ctr Excellence Res Sustainable Chem CERSusChem, Rodovia Washington Luis, Km 235, SP-310, BR-13565905 Sao Carlos, SP - Brazil

^[2] Univ Fed Sao Carlos UFSCar, Dept Quim, Sao Paulo - Brazil

• Tipo de documento: Artigo Científico
• Fonte: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY; v. 2018, n. 40, p. 5467-5476, NOV 1 2018.
• Citações Web of Science: 0

Resumo

Herein we describe a compelling sequential methodology for obtaining optically active alpha-arylmethanols-1,2,3-tri-azoles. The approach is based on the enantioselective alkynylation of aldehydes followed by a one-pot two-step desilylation/ CuI-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC), providing the corresponding products with excellent yields and high levels of enantioselectivity. Furthermore, the click chemistry can be performed without affecting the enantiomeric excess. The application of the reaction has been demonstrated in the synthesis of a 1,2,3-triazole analog of antihistaminic and anticholinergic drug (R)-orphenadrine. (AU)

• Processo FAPESP: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
• Beneficiário: Arlene Gonçalves Corrêa
• Modalidade de apoio: Auxílio à Pesquisa - Programa Centros de Pesquisa em Engenharia
• Processo FAPESP: 13/06558-3 - Catálise metálica assimétrica: preparação de alcoóis quirais e seus derivados a partir de reagentes orgânicos de zinco poli-funcionalizados e aplicação de novos ligantes quirais suportados em nanopartículas magnéticas
• Beneficiário: Ricardo Samuel Schwab
• Modalidade de apoio: Auxílio à Pesquisa - Regular