Synthesis of Azide-alkyne Fragments for ‘Click’ Chemical Applications. Formation of Chiral 1,4-Disubstituted-(β-alkyl)-γ-1,2,3-triazole Scaffolds from Orthogonally Protected Chiral β-Alkyl-trialkylsilyl-γ-pentynyl Azides and Chiral β-Alkyl-γ-pentynyl-alcohols
Oliver D. Montagnat A , Guillaume Lessene B and Andrew B. Hughes A C
+ Author Affiliations
- Author Affiliations
A Department of Chemistry, La Trobe Institute of Molecular Sciences, La Trobe University, Melbourne, Vic. 3086, Australia.
B The Walter and Eliza Hall Institute of Medical Research, 1G Royal Parade, Parkville, Vic. 3052, Australia.
C Corresponding author. Email: a.hughes@latrobe.edu.au
Australian Journal of Chemistry 63(11) 1541-1549 https://doi.org/10.1071/CH10306
Submitted: 16 August 2010 Accepted: 17 September 2010 Published: 11 November 2010
Abstract
A library of chiral γ-pentynyl alcohols and γ-pentynyl azides was made using the SuperQuat auxiliary. Coupling of the free alkynes with the azides by Huisgen 1,3-dipolar cycloaddition provided chiral oligomeric 1,4-disubstituted-1,2,3-triazoles as possible peptidomimetic compounds.
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