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通过 α-氨基膦酸酯的芳基氮杂-Claisen 重排反应立体选择性合成乙烯基膦酸酯。

Stereoselective synthesis of vinylphosphonates through aromatic aza-Claisen rearrangement of α-aminophosphonates.

机构信息

Department of Chemistry, Institute for Advanced Studies in Basic Sciences (IASBS), Gava Zang, Zanjan 45137-66731, Iran.

School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.

出版信息

Chem Commun (Camb). 2023 Jun 6;59(46):7076-7079. doi: 10.1039/d3cc01669b.

Abstract

A novel and convenient approach for the synthesis of vinyl phosphonates has been developed, utilizing an aromatic aza-Claisen rearrangement of β,γ-unsaturated α-aminophosphonates. The synthetic utility of this method was further examined in a gram-scale synthesis. The DFT calculations have provided insights into the basis of the reaction mechanism.

摘要

一种新颖且便捷的合成乙烯基膦酸酯的方法已经被开发出来,该方法利用了β,γ-不饱和α-氨基膦酸酯的芳基氮杂-Claisen 重排反应。该方法的合成实用性在克级规模的合成中得到了进一步的检验。DFT 计算为反应机理提供了深入的见解。

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