CAREER: Chiral Catalysts for Enantioselective Photoredox-Catalyzed Carbon-Carbon Bond-Forming Reactions

职业：用于对映选择性光氧化还原催化碳-碳键形成反应的手性催化剂

• 批准号: 2337159
• 负责人: Ming-Yu Ngai
• 金额: $ 67.5万
• 依托单位: Purdue University
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 2023
• 资助国家: 美国
• 起止时间: 2023-09-01 至 2025-06-30
• 项目状态: 未结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=2337159&HistoricalAwards=false
• 关键词: CAREER; Chiral; Catalysts; Enantioselective; Photoredox

In this project, funded by the Chemical Catalysis program of the NSF Chemistry Division, Professor Ming-Yu Ngai of the Department of Chemistry at Stony Brook University develops new and efficient photochemical reactions to prepare chiral organic molecules. Chiral molecules exist in specific configurations known as enantiomers. Each configuration has the same atoms, but arranged spatial in a different order, this results in different chemical properties. The goal of this project is to design and optimize novel catalysts to yield specific enantiomers. It is often important to select one specific enantiomer because the other is ineffective or harmful. New synthetic methods developed in this research may have applications in the syntheses of pharmaceuticals, agrochemicals, and materials chemistry. An integral part of this program is to recruit and prepare a diverse STEM (Science, Technology, Engineering and Mathematics) workforce to advance the frontiers of science. This project provides students with opportunities for industrial training through collaboration with a major pharmaceutical company. Professor Ngai establishes a hands-on synthetic module to introduce organic synthesis and molecular photochemistry to high school students and a summer industrial internship program to better prepare graduate students for future careers in advanced chemical manufacturing.Over half of all top-selling drugs are marketed as single enantiomers; often because the other enantiomer is ineffective or harmful. As a consequence, catalytic reactions that can readily increase the structural complexity of molecules while maintaining control of the stereochemistry of the newly formed stereocenters are of importance in drug discovery and development. Visible-light photoredox catalysis has emerged as a potentially powerful tool in organic synthesis. This catalysis has changed the way in which chemists approach some difficult synthetic problems. Precise stereocontrol of photocatalytic reactions remains a significant challenge. This research focuses on the design and development of chiral Lewis acid catalysts which enable stereoselective, visible-light mediated photoredox catalysis. These new catalysts are applied to enantioselective cross-coupling reactions of carbonyl and iminyl derivatives with alkenes. This project generates a library of novel tridentate chiral ligands and chiral catalysts that guide the development of asymmetric chemical transformations. The hands-on organic synthesis activities developed by Professor Ngai enrich the educational experience of high school students and encourage them to pursue advanced degrees in STEM (Science, Technology, Engineering and Mathematics) education. These activities also provide training opportunities to pre-service chemistry teachers for their professional development. An established industrial collaboration and a summer internship program for graduate students at Boehringer Ingelheim further support career development in advanced chemical manufacturing.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.

在这个项目中，由美国国家科学基金会化学部化学催化项目资助，石溪大学化学系的 Ming-Yu Ngai 教授开发了新的高效光化学反应来制备手性有机分子。 手性分子以称为对映体的特定构型存在。 每种构型都具有相同的原子，但以不同的顺序空间排列，这导致了不同的化学性质。该项目的目标是设计和优化新型催化剂以产生特定的对映体。 选择一种特定的对映体通常很重要，因为另一种对映体无效或有害。本研究开发的新合成方法可能在药物、农用化学品和材料化学的合成中得到应用。该计划的一个组成部分是招募和准备一支多元化的 STEM（科学、技术、工程和数学）劳动力队伍，以推进科学前沿。该项目通过与一家大型制药公司合作，为学生提供工业培训的机会。 魏教授建立了一个实践合成模块，向高中生介绍有机合成和分子光化学，并建立了暑期工业实习计划，以便更好地为研究生在先进化学制造领域的未来职业做好准备。所有最畅销药物的一半以上以单一对映体；通常是因为另一种对映体无效或有害。因此，催化反应可以轻松增加分子的结构复杂性，同时保持对新形成的立体中心的立体化学的控制，这对于药物发现和开发非常重要。可见光光氧化还原催化已成为有机合成中潜在的强大工具。 这种催化作用改变了化学家解决一些困难合成问题的方式。光催化反应的精确立体控制仍然是一个重大挑战。本研究重点是手性路易斯酸催化剂的设计和开发，该催化剂能够实现立体选择性、可见光介导的光氧化还原催化。这些新型催化剂适用于羰基和亚氨基衍生物与烯烃的对映选择性交叉偶联反应。该项目生成了一个新型三齿手性配体和手性催化剂库，指导不对称化学转化的发展。魏教授开发的有机合成实践活动丰富了高中生的教育经验，并鼓励他们攻读STEM（科学、技术、工程和数学）教育的高级学位。这些活动还为职前化学教师的专业发展提供培训机会。勃林格殷格翰已建立的工业合作和研究生暑期实习计划进一步支持先进化学制造领域的职业发展。该奖项反映了 NSF 的法定使命，并通过使用基金会的智力价值和更广泛的影响审查标准进行评估，被认为值得支持。