New Methods for the Asymmetric Synthesis of Amines

在这项由化学系化学催化计划资助的项目中，耶鲁大学的乔纳森·埃尔曼教授正在开发高效的不对称合成手性胺的新策略，手性胺是制药、农用化学品和新材料中的重要主题。这项工作的更广泛的影响包括开发新的实用方法来不对称合成适用于药物、农用化学品和材料制备的重要手性胺类。此外，Ellman教授定期参与耶鲁大学的科学、技术和研究学者计划，为代表不足的少数族裔和女性科学家提供在他的实验室进行研究的机会。埃尔曼教授还参与了耶鲁大学科学途径计划，该计划积极支持纽黑文对科学感兴趣的初中生和高中生。该研究计划包括两个主要部分。一部分依赖于实际的不对称合成氨基硼酸衍生物，通过过渡金属催化与各种不同的碳亲电体反应，得到有价值的手性胺产品。在第二个研究领域中，不对称有机催化被用来偶联亲核剂和取代的硝基烯烃。硝基的还原然后得到手性支化胺产品。这一策略的一个关键步骤是对映体选择性硝酸盐质子化，这是以前没有研究过的。

AbstractIn this project funded by the Chemical Catalysis Program of the Chemistry Division, Professor Jonathan Ellman of Yale University is developing efficient new strategies for the asymmetric synthesis of chiral amines, which are important motifs in pharmaceuticals, agrochemicals and new materials. The broader impacts of this work include the potential for the development of new and practical methods for the asymmetric synthesis of important classes of chiral amines applicable to the preparation of pharmaceuticals, agrochemical and materials. In addition, Professor Ellman regularly participates in Yale's Science, Technology and Research Scholars program by providing opportunities for underrepresented minority and women scientists to carry out research in his laboratory. Professor Ellman also participates in the Yale University Science Pathways program, which actively supports New Haven middle and high school students interested in science.The research program has two main parts. One part relies on the practical asymmetric synthesis of aminoboronic acid derivatives that are engaged through transition metal catalysis to react with a variety of different carbon electrophiles to give valuable chiral amine products. In the second research area asymmetric organocatalysis is used to couple nucleophiles with substituted nitroalkenes. Reduction of the nitro group then provides chiral branched amine products. A key step in this strategy is enantioselective nitronate protonation, which has not previously been investigated.