3-Imidoallenylphosphonates: In Situ Formation and β-Alkoxylation

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• 作者：Jan K. E. T. Berton ; Thomas S. A. Heugebaert ; Wouter Debrouwer ; Christian V. Stevens
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：January 15, 2016
• 年：2016
• 卷：18
• 期：2
• 页码：208-211
• 全文大小：306K
• ISSN：1523-7052

文摘

3-Imidoallenylphosphonates, allenes bearing both an electron-withdrawing and -donating group, were isolated for the first time. An alkoxy substituent was introduced into these unprecedented intermediates in a one-pot approach, yielding β-functionalized aminophosphonates in excellent yields and short reaction times. The mechanistic insights gained are important additions to the domain of allene chemistry. Addition of biologically important molecules, including monoglycerides, amino acids, and nucleosides, proves the general applicability of the developed method.