Asymmetric Synthesis with Boronic Esters

本研究的重点是利用硼酸化学开发不对称合成方法。将硼酸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代硼烷，将用于仲胺的不对称合成和开发新的碳-碳键形成反应。将探索以富含对映体的硼酸为催化剂，以二烷基二氟硼盐为捕捉剂的催化反应。在具有代表性的天然产物的全合成中，将利用构建邻近的含烷基立体中心、独特的含胺立体中心和高度官能化的四元环和五元环的能力。通过这次续展奖，有机和高分子化学计划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教授将专注于开发使用硼酸酯化学的不对称合成方法。该研究领域非常适合培养研究生，研究结果可能会对制药和农业产生影响。

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.