Lewis Acid Mediated Tandem Reaction of Propargylic Alcohols with Hydroxylamine Hydrochloride To Give α,β-Unsaturated Amides and Alkenyl Nitriles

We
have developed a highly selective method for the synthesis of
α,β-unsaturated amides and alkenyl nitriles from readily
available propargylic alcohols. The reaction proceeded smoothly under
the neutral conditions with hydroxylamine hydrochloride (NH2OH·HCl) as the nitrogen source. The development of these new
strategies has significantly extended the application of hydroxylamine
hydrochloride to the chemistry of propargylic alcohols. Moreover,
both secondary and tertiary alcohols have been highly regioselectively
transformed to the desired products with good functional group compatibility.