A Synthon Approach to Selective Fluorination Using Vinyl- and Propargylphosphonates

使用乙烯基膦酸酯和炔丙基膦酸酯进行选择性氟化的 Synthon 方法

• 批准号: 9711062
• 负责人: Gerald Hammond
• 金额: $ 20.17万
• 依托单位: University of Massachusetts, Dartmouth
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 1997
• 资助国家: 美国
• 起止时间: 1997-08-01 至 2001-01-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=9711062&HistoricalAwards=false
• 关键词: Synthon; Approach; Selective; Fluorination; Using

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.

本研究的重点是第二代含氟膦酸盐合成子的开发。为此，将结合固相氟化研究合成氟化的伽马-硅基-α-氟炔基膦酸酯，使用膦酸根作为离开基团，并合成环状α-氟-和α，α-二氟炔基膦酸酯。这项研究的长期目标包括固相氟掺入GEM-二氟丙叉基团，合成核苷酸的含氟膦类似物，合成杂环α-氟代丙叉基膦酸酯，以及在α-氟丙叉基膦酸基的氟甲基碳上传递手性。通过这一更新的本科生机构研究(RUI)奖，合成有机计划正在支持达特茅斯大学马萨诸塞大学化学系的Gerald B.Hammond博士的研究。哈蒙德教授将专注于开发一组被称为氟磷酸盐合成子的试剂。这些分子是用途广泛的合成中间体，可作为生物磷酸盐(一类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。