Design, Development and Exploration of New Chiral Spirocyclic Ligands and Catalysts for Asymmetric Catalysis

新型手性螺环配体和不对称催化催化剂的设计、开发和探索

基本信息

批准号：
1955069
负责人：
Pavel Nagorny
金额：
$ 38万
依托单位：
Regents of the University of Michigan - Ann Arbor
依托单位国家：
美国
项目类别：
Standard Grant
财政年份：
2020
资助国家：
美国
起止时间：
2020-08-15 至 2023-07-31
项目状态：
已结题

来源：
https://www.nsf.gov/awardsearch/showAward?AWD_ID=1955069&HistoricalAwards=false
关键词：
Design Development Exploration New Chiral

项目摘要

With this award, the Chemical Catalysis Program of the NSF Division of Chemistry is supporting the research of Dr. Pavel Nagorny of the Department of Chemistry at the University of Michigan. Dr. Nagorny and his research team are developing catalyst scaffolds that can control how molecules interact to produce favored enantiomeric products. Enantiomers are molecules that have similar structures but are mirror images of each other (i.e. a right hand and a left hand). Different enantiomers can have distinct characteristics including therapeutic potency and properties, which is why there is a critical need for catalysts that can selectively form these molecules. The Nagorny research group has previously identified a new type of catalyst that is highly active towards controlling enantioselectivity and is easily tunable towards new types of reactions. Professor Nagorny and his students are currently investigating how these catalysts work and optimizing them for the synthesis of compound fragments that are currently found in bioactive molecules. In addition, the Nagorny group is developing heterogeneous analogues of these catalysts to improve recyclability and sustainability. These studies are being used to train a diverse group of graduate and undergraduate students. Professor Nagorny and his students are also developing instructional safety videos to improve the learning experience of students at the University of Michigan and beyond.Improvements in asymmetric catalysis are critically important for the synthesis of bioactive molecules. To address this need, Dr. Pavel Nagorny and his research group are expanding the repertoire of existing spirocyclic ligands for iridium-catalyzed hydrogenations by exploring a new C2-symmetric chiral scaffold (SPIROL). These ancillary groups possess the key structural features found in the most popular and best-performing chiral spirocyclic ligands and catalysts, but are also easy to synthesize and tune. Simultaneously, the Nagorny group is also working to improve the process efficiency and sustainability associated with the use of spirocyclic catalysts by developing immobilized variants. Immobilized chiral spirocyclic phosphoric acids are being optimized for asymmetric transformations in continuous flow. These studies are advancing tools and processes needed to accelerate asymmetric synthesis.This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.

通过此奖项，NSF化学部的化学催化计划支持密歇根大学化学系的Pavel Nagorny博士的研究。 Nagorny博士和他的研究团队正在开发催化剂脚手架，这些催化剂脚手架可以控制分子如何相互作用以生产受欢迎的对映体产品。对映异构体是具有相似结构但彼此镜像的分子（即右手和左手）。不同的对映异构体可以具有不同的特征，包括治疗效力和特性，这就是为什么对可以选择性形成这些分子的催化剂至关重要的原因。 Nagorny研究小组先前已经确定了一种新型的催化剂，该催化剂非常活跃，可以控制对映选择性，并且很容易对新的反应进行调整。 Nagorny教授和他的学生目前正在研究这些催化剂如何工作并优化它们，以合成当前在生物活性分子中发现的复合片段。此外，Nagorny组正在开发这些催化剂的异质类似物，以提高可回收性和可持续性。这些研究被用来培训各种各样的研究生和本科生。 Nagorny教授和他的学生还正在开发教学安全视频，以改善密歇根大学及其他地区的学生的学习经验。不对称催化的进展对于合成生物活性分子至关重要。为了满足这一需求，Pavel Nagorny博士及其研究小组正在通过探索新的C2-对称性手性支架（Spirol）来扩展现有的螺旋环体配体的曲目，以促进虹膜催化的氢化。这些辅助组具有在最受欢迎，表现最佳的手性螺旋形配体和催化剂中发现的关键结构特征，但也很容易合成和调整。同时，Nagorny组也在努力通过开发固定的变体来提高与使用螺旋细胞催化剂相关的过程效率和可持续性。固定的手性螺旋环磷酸正在优化连续流中的不对称转化。这些研究是加速不对称综合所需的工具和流程。该奖项反映了NSF的法定任务，并且使用基金会的知识分子优点和更广泛的影响标准，被认为值得通过评估来获得支持。