1 research outputs found
Direct Substitution of Arylalkynyl Carbinols Provides Access to Diverse Terminal Acetylene Building Blocks
To
develop next generation antifolates for the treatment of trimethoprim-resistant
bacteria, synthetic methods were needed to prepare a diverse array
of 3-aryl-propynes with various substitutions at the propargyl position.
A direct route was sought whereby nucleophilic addition of acetylene
to aryl carboxaldehydes would be followed by reduction or substitution
of the resulting propargyl alcohol. The direct reduction, methylation,
and dimethylation of these readily available alcohols provide efficient
access to this uncommon functional array. In addition, an unusual
silane exchange reaction was observed in the reduction of the propargylic
alcohols