Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Silesian University of Technology, B. Krzywoustego 4, 44-100 Gliwice, Poland.
Biotechnology Center of Silesian University of Technology, B. Krzywoustego 8, 44-100 Gliwice, Poland.
Molecules. 2019 Sep 19;24(18):3405. doi: 10.3390/molecules24183405.
In this study, Michaelis-Arbuzov-type reaction of 1-imidoalkyltriarylphosphonium salts with phosphites, phosphonites, and phosphinites was used in the synthesis of a wide range of phosphorus analogs of α-amino acids such as 1-imidoalkylphosphonates, 1-imidoalkylphosphinates, and 1-imidoalkylphosphine oxides. Large differences were observed in the reactivity of substrates depending on their structure, especially on the type of phosphonium moiety and -protecting group. The conditions under which the expected products can be obtained in good to excellent yields have been developed. Mechanistic aspects of the transformation have been provided.
在这项研究中，作者使用了 1-亚氨基烷基三芳基鏻盐与亚膦酸酯、次膦酸酯和亚磷酸酯的 Michaelis-Arbuzov 型反应，合成了广泛的α-氨基酸的磷类似物，如 1-亚氨基烷基膦酸酯、1-亚氨基烷基膦酸盐和 1-亚氨基烷基氧化膦。底物的反应性因结构而异，尤其是磷翁部分和保护基的类型，观察到了很大的差异。已经开发出了可以获得预期产物的良好到优秀产率的条件。还提供了转化的机制方面。
