Asymmetric Synthesis with Boronic Esters

硼酸酯的不对称合成

• 批准号: 0353145
• 负责人: Donald Matteson
• 金额: $ 33万
• 依托单位: Washington State University
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 2004
• 资助国家: 美国
• 起止时间: 2004-02-15 至 2007-01-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=0353145&HistoricalAwards=false
• 关键词: Asymmetric; Synthesis; Boronic; Esters

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.

本研究的重点是发展不对称合成方法，使用硼酸化学。将硼酸酯转化为稳定的烷基三氟硼酸酯，然后转化为高反应性的烷基二卤代硼烷将用于仲胺的不对称合成和新的碳-碳键形成反应的发展。将探索涉及对映体富集的硼酸作为催化剂和二烷基二氟硼酸盐作为反应产物的捕集剂的催化作用。有机和大分子化学计划将支持Donald S.博士的研究，该计划将在天然产物的全合成中开发具有代表性的邻位烷基立体中心，独特的胺立体中心和高度官能化的四元和五元环。华盛顿州立大学化学系的Matteson说。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研究生的培养，研究结果可能对制药和农业行业产生影响。