Synthesis of Azide-Alkyne Fragments for "Click" Chemical Applications. Part 2. Formation of Oligomers from Orthogonally Protected Chiral Trialkylsilylhomopropargyl Azides and Homopropargyl Alcohols
Oliver D Montagnat, Guillaume Lessene, Andrew B Hughes
The Journal of Organic Chemistry | AMER CHEMICAL SOC | Published : 2010
A small library of chiral, beta(3)-substituted homopropargyl alcohols and chiral beta(3)-substituted trimethylsilylhomopropargyl azides were generated starting from natural l-amino acids. The free alkynes and azides were then coupled, using a Huisgen 1,3-dipolar cycloaddition, to provide chiral oligomeric 1,4-disubstituted-1,2,3-triazoles as potential peptidomimetic compounds. The work is an extension to the previous synthesis of racemic, orthogonally protected 1,4-disubstituted-1,2,3-triazoles from the corresponding alpha-substituted propargyl alcohols and alpha-substituted trialkylsilylpropargyl azides.
One of us (O.M.) would like to thank the Australian Government for the grant of an Australian Postgraduate Award (APA).