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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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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]
Total Authors: 6
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
Total Affiliations: 2
Document type: Journal article
Source: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY; 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 type: 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 type: Regular Research Grants