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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.

有了这个奖项，NSF化学部的化学催化计划正在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支架，可以控制分子如何相互作用以产生有利的对映体产物。对映异构体是具有相似结构但彼此成镜像（即右手和左手）的分子。不同的对映异构体可以具有不同的特征，包括治疗效力和性质，这就是为什么迫切需要可以选择性地形成这些分子的催化剂。Nagorny研究小组先前已经确定了一种新型催化剂，该催化剂对控制对映选择性具有高度活性，并且易于对新型反应进行调节。Nagorny教授和他的学生目前正在研究这些催化剂如何工作，并优化它们以合成目前在生物活性分子中发现的化合物片段。此外，Nagorny集团正在开发这些催化剂的多相类似物，以提高可回收性和可持续性。这些研究被用来培训一批多样化的研究生和本科生。Nagorny教授和他的学生还在开发教学安全视频，以改善密歇根大学及其他大学学生的学习体验。不对称催化的改进对于生物活性分子的合成至关重要。为了满足这一需求，Pavel Nagorny博士和他的研究小组正在通过探索新的C2对称手性支架（SPIROL）来扩展现有的铱催化氢化螺环配体的库。这些辅助基团具有在最流行和性能最好的手性螺环配体和催化剂中发现的关键结构特征，但也易于合成和调节。同时，Nagorny集团还致力于通过开发固定化变体来提高与螺环催化剂使用相关的工艺效率和可持续性。固定化手性螺环磷酸正被优化用于连续流动中的不对称转化。该奖项反映了NSF的法定使命，并被认为值得通过使用基金会的知识价值和更广泛的影响审查标准进行评估来支持。