[2,3]-Sigmatropic Rearrangement of Ynamides: Preparation of 伪-Amino Allenephosphonates

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• 作者：Filipe Gomes ; Antoine Fadel ; Nicolas Rabasso
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：June 15, 2012
• 年：2012
• 卷：77
• 期：12
• 页码：5439-5444
• 全文大小：308K
• 年卷期：v.77,no.12(June 15, 2012)
• ISSN：1520-6904

文摘

伪-Amino allenephosphonates were easily prepared in two steps from protected amines, propargyl alcohols, and chlorophosphites. First, ynamides were synthesized from unprotected 1-bromopropargyl alcohols using a copper(II) catalyzed coupling reaction. In the second step, the previously prepared ynamides were transformed directly to allenes through a [2,3]-sigmatropic rearrangement of propargyl phosphites. This efficient method led to the formation of a series of 伪-amino allenephosphonates with diverse substituents on the amine, the phosphonate, and the allene moieties.