A Synthon Approach to Selective Fluorination Using Vinyl- and Propargylphosphonates

本研究的重点涉及第二代的开发 氟代膦酸盐。为此，合成氟化的 γ-甲硅烷基-α-氟代炔膦酸酯与固体 相分离研究，使用膦酸酯作为离去基团， 环状α-氟代和α，α-二氟代炔合成 将进行膦酸盐。 研究的长期目标 包括偕二氟炔丙基固相氟掺入 单元，核苷酸的氟化膦酸类似物的合成， 杂环α-氟膦酸酯的合成及传递 α-氟炔丙基中氟亚甲基碳上的手性 膦酸盐。 随着这一更新研究在本科院校 (RUI)奖，合成有机计划是支持研究 杰拉尔德B博士。密歇根大学化学系的哈蒙德说， 马萨诸塞州，达特茅斯。 哈蒙德教授将把他的工作重点放在 开发了一组被称为氟代膦酸盐的试剂。 这些分子是多用途的合成中间体， 氟代膦酸酯是一类重要的生物磷酸盐模拟物， 以及作为含氟的配体用于制备有机氟化合物 化合物. 拟议的研究将主要由以下方面进行： 本科生。

The focus of this research involves the development of second generation fluorophosphonate synthons. To this end, the synthesis of fluorinated gamma-silyl-alpha-fluoroalkyne phosphonates in conjunction with solid phase fluorination studies, the use of phosphonate as a leaving group and the synthesis of cyclic alpha-fluoro- and alpha, alpha-difluoroalkyne phosphonates will be carried out. The long-term goals of the research include solid phase fluorine incorporation of a gem-difluoropropargyl unit, synthesis of fluorinated phosphonic analogs of nucleotides, synthesis of heterocyclic alpha-fluoro phosphonates and transmission of chirality at the fluoromethylene carbon in alpha-fluorpropargyl phosphonates. With this renewal Research in Undergraduate Institutions (RUI) award, the Synthetic Organic Program is supporting the research of Dr. Gerald B. Hammond of the Department of Chemistry at the University of Massachusetts, Dartmouth. Professor Hammond will focus his work on developing a group of reagents known as fluorophosphonate synthons. These molecules are versatile synthetic intermediates as precursors to fluorophosphonates , an important group of biological phosphate mimics, and as fluorine containing synthons for the preparation of organofluoro compounds. The proposed research will be carried out, in the main, by undergraduate students.