Asymmetric Synthesis with Boronic Esters

本研究的重点是发展硼酸化学合成的不对称方法。硼酯转化为稳定的烷基三氟硼酸盐，然后转化为高活性的烷基二卤硼烷，将用于不对称合成仲胺和开发新的碳-碳成键反应。探讨了以富对映体硼酸为催化剂，双烷基双氟硼酸盐为反应产物捕集剂的催化反应。构建邻烷基立体中心、独特的胺立体中心和高度功能化的四元环和五元环的能力将在具有代表性的天然产物的全合成中得到利用。有了这个更新奖，有机和大分子化学项目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。Matteson教授将专注于利用硼酯化学发展不对称合成方法。该研究领域非常适合培养研究生，研究结果可能对制药和农业工业产生影响。

The focus of this research is the development of asymmetric methods for synthesis using boronic acid chemistry. Conversion of boronic esters to stable alkyltrifluoroborates and then on to highly reactive alkyldihaloboranes will be used for the asymmetric synthesis of secondary amines and development of new carbon-carbon bond forming reactions. Catalysis involving an enantioenriched boronic acid as the catalyst and a dialkyl bifluoroborate salt as a trap for the reaction products will be explored. The ability to construct vicinal alkyl-bearing stereocenters, unique amine-bearing stereocenters, and highly functionalized four- and five-membered rings will be exploited in the total synthesis of representative natural products.With this renewal award, the Organic and Macromolecular Chemistry 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 developing asymmetric synthesis methodology using boronic ester chemistry. The area of research is excellent for the training of graduate students and the results of the research could have implications for the pharmaceutical and agricultural industries.