Asymmetric Synthesis with Boronic Esters

本研究的重点是硼酸酯在不对称合成中的应用。新的化学，这应该是有用的收敛合成将进行研究，包括一种新型的烯丙基基团转移从一个硼原子到另一个，和连接卤代硼酸酯羧酸酯烯醇化物。这两种方法都在连接点处产生新的手性中心，可能具有高立体选择性。卤代硼酸酯的环化将用于制备具有手性控制的四元和五元环。将研究使用乙烯基硼中间体的分子内Diels-Alder反应。在主要研究者的实验室中发现了一种温和的生成烷氧基硼氢化物的方法，该方法将被用作新的廉价不对称还原剂的途径。%有了这个更新奖，合成有机计划是支持博士唐纳德S。华盛顿州立大学化学系的马特森说。Matteson教授的工作重点是在不对称合成中使用硼酸酯作为生产手性分子的一般方法。

The focus of this research is the use of boronic esters in asymmetric synthesis. New chemistry which should be useful for convergent syntheses will be studied, including a new type of allylic group transfer from one boron atom to another, and connection of halo boronic esters to carboxylic ester enolates. Both of these yield a new chiral center at the connection point, potentially with high stereoselectivity. Cyclization of halo boronic esters will be used for making four- and five-membered rings with chirality control. Intramolecular Diels-Alder reactions using vinyl boron intermediates will be investigated. A mild method of generating alkoxyborohydrides, discovered in the Principal Investigator's laboratory, will be utilized as a route to new and inexpensive asymmetric reducing agents. %%% With this Renewal award, the Synthetic Organic Program is supporting the research of Dr. Donald S. Matteson of the Department of Chemistry at Washington State University. Professor Matteson will focus his work on the use of boronic esters in asymmetric synthesis as a general method for the production of chiral molecules.