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

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• 作者：Ya-Ping Han ; Xian-Rong Song ; Yi-Feng Qiu ; Xin-Hua Hao ; Jia Wang ; Xin-Xing Wu ; Xue-Yuan Liu ; Yong-Min Liang
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：September 18, 2015
• 年：2015
• 卷：80
• 期：18
• 页码：9200-9207
• 全文大小：502K
• ISSN：1520-6904

文摘

We have developed a highly selective method for the synthesis of 伪,尾-unsaturated amides and alkenyl nitriles from readily available propargylic alcohols. The reaction proceeded smoothly under the neutral conditions with hydroxylamine hydrochloride (NH₂OH路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.