Asymmetric Synthesis with Boronic Esters

本研究的重点是硼酯在不对称合成中的应用。将研究有助于会聚合成的新化学，包括一种新型的烯丙基基团从一个硼原子转移到另一个硼原子，以及晕硼酯与羧酸酯烯醇酯的连接。这两种方法都能在连接点产生新的手性中心，具有潜在的高立体选择性。环硼酯的环化将用于制造具有手性控制的四元和五元环。分子内Diels-Alder反应使用乙烯基硼中间体将进行研究。在首席研究员的实验室中发现的一种生成烷氧硼氢化物的温和方法，将被用作制造新的廉价不对称还原剂的途径。有了这个更新奖，合成有机项目正在支持华盛顿州立大学化学系的唐纳德·s·马特森博士的研究。马特森教授将把他的工作重点放在硼酯在不对称合成中的应用上，作为一种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.