New Strategies for the Enantioselective Synthesis of Fluorinated Molecules

本研究的重点是开发新的立体选择性合成特异性氟化分子。本文研究了各种含氟构件的反应性和选择性，以及氟的存在对这些因素的影响。为此目的，将探讨氟化烯酮、烯酮等价物或其衍生产品的立体选择性反应性。具体方面包括氟烯酮在环加成反应中的反应性研究、氟化过渡金属有机金属配合物作为氟烯酮替代品的制备、使用光学纯氟化β -内酰胺作为构建单元、使用光学纯氟化环丁酮作为中间体以及使用氟化C，O-二乙烯基烯酮作为构建单元来合成氟化烯烃。有了这个奖项，合成有机项目支持了纽约州立大学奥尔巴尼分校化学系的约翰·t·韦尔奇博士的研究。韦尔奇教授将把他的工作重点放在开发新的立体选择性合成特异性氟化分子上。该策略将使用反应性，功能化氟化中间体的结构，可以经历各种进一步的立体选择转化。这类体系包括氟化酮、β -内酰胺和环丁酮。所开发的方法将允许合成光学纯氟化化合物，这些化合物可以用作各种机械和生物问题以及材料应用中的探针。

The focus of this research is the development of new stereoselective syntheses of specifically fluorinated molecules. The work studies the reactivity and selectivity of various fluorinated building blocks and how these factors are effected by the presence of fluorine. Toward this end the stereoselective reactivity of fluorinated ketenes, ketene equivalents or products derived from them will be explored. Specific aspects include a study of the reactivity of fluoroketenes in cycloaddition reactions, preparation of fluorinated transition metal organometallic complexes as fluoroketene surrogates, use of optically pure fluorinated beta-lactams as building blocks, use of optically pure fluorinated cyclobutanones as intermediates, and use of fluorinated C,O- disilylketenes as building blocks for the synthesis of fluorinated olefins. With this award, the Synthetic Organic Program is supporting the research of Dr. John T. Welch of the Department of Chemistry at the SUNY Albany. Professor Welch will focus his work on the development of new stereoselective syntheses of specifically fluorinated molecules. This strategy will use the construction of reactive, functionalized fluorinated intermediates that can undergo a variety of further stereoselective transformations. Such systems include fluorinated ketenes, beta-lactams and cyclobutanones. The methodology developed will allow the synthesis of optically pure fluorinated compounds that can be used as probes in a variety of mechanistic and biological problems, as well as materials applications.