New Strategies for the Enantioselective Synthesis of Fluorinated Molecules

本研究的重点是发展新的立体选择性合成特定的氟化分子。 这项工作研究了各种氟化结构单元的反应性和选择性，以及氟的存在如何影响这些因素。 为此，将探索氟化烯酮、烯酮等价物或由它们衍生的产物的立体选择性反应性。 具体方面包括氟代烯酮在环加成反应中的反应性的研究，作为氟代烯酮替代物的氟化过渡金属有机金属络合物的制备，光学纯的氟化β-内酰胺作为结构单元的用途，光学纯的氟化环丁酮作为中间体的用途，以及氟化C，O-二甲硅烷基烯酮作为用于合成氟化烯烃的结构单元的用途。 有了这个奖项，合成有机计划是支持博士约翰T。纽约州立大学奥尔巴尼化学系的韦尔奇说。 韦尔奇教授将专注于他的工作，特别是氟化分子的新的立体选择性合成的发展。 该策略将使用反应性的、官能化的氟化中间体的构造，所述氟化中间体可以进行各种进一步的立体选择性转化。 此类体系包括氟化烯酮、内酰胺和环丁酮。 开发的方法将允许合成光学纯的氟化化合物，可用作探针在各种机械和生物学问题，以及材料应用。

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.