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

Author(s)

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]

Affiliation

^[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

• Document type: Journal article
• Source: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY; v. 2018, n. 40, p. 5467-5476, NOV 1 2018.
• Web of Science Citations: 0

Abstract

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)

• FAPESP's process: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
• Grantee: Arlene Gonçalves Corrêa
• Support Opportunities: Research Grants - Research Centers in Engineering Program
• FAPESP's process: 13/06558-3 - Asymmetric catalysis: preparation of chiral alcohols and their derivatives from highly functionalized organozinc reagents and application of new chiral ligands supported on magnetic nanoparticles
• Grantee: Ricardo Samuel Schwab
• Support Opportunities: Regular Research Grants