Li Shunzi, Whitehead John K, Hammer Robert P
Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, Louisiana 70803, USA.
J Org Chem. 2007 Apr 13;72(8):3116-8. doi: 10.1021/jo070266p. Epub 2007 Mar 22.
A convenient and efficient method has been developed for the preparation of 9-fluorenylmethoxycarbonyl (Fmoc)-protected 1-aminoalkylphosphinic acids. Reproducible procedures for the synthesis and purification of free alpha-amino H-phosphinates are provided. Protection of free amino phosphinates as the N-Fmoc derivative was achieved by in situ trimethylsilylation of aminoalkylphosphinic acids, which then reacted with Fmoc-Cl to provide corresponding products in excellent yields and in high purity after simple extractive isolation. Mechanistic aspects of the silylation are discussed, and the application of the procedure to another class of amino phosphorus acids is presented.
已开发出一种便捷高效的方法来制备9-芴甲氧羰基（Fmoc）保护的1-氨基烷基次膦酸。提供了游离α-氨基H-次膦酸酯合成和纯化的可重现程序。通过氨基烷基次膦酸的原位三甲基硅烷化将游离氨基次膦酸酯保护为N-Fmoc衍生物，然后与Fmoc-Cl反应，经简单萃取分离后可得到高产率和高纯度的相应产物。讨论了硅烷化的机理，并介绍了该程序在另一类氨基磷酸中的应用。
