New Methods for the Asymmetric Synthesis of Amines

摘要在耶鲁大学化学系化学催化计划资助的这个项目中，Jonathan Ellman教授正在开发高效的手性胺的不对称合成新策略，手性胺是药物、农药和新材料中的重要基元。这项工作的更广泛的影响包括开发新的和实用的方法，用于不对称合成适用于制备药物，农用化学品和材料的重要类别的手性胺的潜力。此外，埃尔曼教授定期参加耶鲁大学的科学，技术和研究学者计划，为代表性不足的少数民族和女性科学家提供在他的实验室开展研究的机会。Ellman教授还参加了耶鲁大学科学途径项目，该项目积极支持纽黑文对科学感兴趣的初中和高中学生。该研究项目有两个主要部分。一部分依赖于氨基硼酸衍生物的实际不对称合成，这些衍生物通过过渡金属催化与各种不同的碳亲电试剂反应，得到有价值的手性胺产物。在第二个研究领域，不对称有机催化用于亲核试剂与取代硝基烯烃的偶联。然后硝基的还原提供手性支化胺产物。在这一战略中的一个关键步骤是对映选择性硝基质子化，这是以前没有被调查。

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.