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

The Journal of Organic Chemistry
Ya-Ping HanYong-Min Liang

Abstract

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.

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Citations

Sep 30, 2016·Organic Letters·Vinoth Kumar Chenniappan, Ronald J Rahaim
Jul 21, 2017·Organic Letters·Kai HuangYanguang Wang
Dec 6, 2017·Chemistry : a European Journal·Mary M JackmanSteven L Castle
Jul 22, 2017·The Journal of Organic Chemistry·Lang SunYanguang Wang

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