A Synthon Approach to Selective Fluorination Using Vinyl- and Propargylphosphonates

本研究的重点涉及第二代氟膦酸盐合成子的开发。为此目的，将结合固相氟化研究、使用膦酸盐作为离去基以及合成环-氟-和- -二氟炔膦酸盐，进行氟化γ -硅- - -氟炔膦酸盐的合成。该研究的长期目标包括在固相氟中加入宝石-二氟丙炔单元、合成核苷酸的氟化膦类似物、合成杂环α -氟膦酸盐以及α -氟丙炔膦酸盐中氟甲基碳的手性传递。有了这个更新的本科院校研究（RUI）奖，合成有机项目将支持马萨诸塞大学达特茅斯分校化学系的杰拉尔德·b·哈蒙德博士的研究。哈蒙德教授将专注于开发一组被称为氟膦酸合子的试剂。这些分子是多用途的合成中间体，作为氟膦酸盐（一组重要的生物磷酸盐模拟物）的前体，以及用于制备有机氟化合物的含氟合成子。拟议的研究将主要由本科生进行。

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.