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; 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.

在该项目中，由NSF化学部的化学催化计划资助，Stony Brook University化学系的Ming-Yu Ngai教授开发了新的有效的光化学反应，以准备手性有机分子。 手性分子以称为对映异构体的特定构型存在。 每种构型具有相同的原子，但以不同顺序排列的空间，这会导致不同的化学性质。该项目的目的是设计和优化新型催化剂，以产生特定的对映异构体。 选择一个特定的对映异构体通常很重要，因为另一个对映异构体无效或有害。这项研究中开发的新合成方法可能在药物，农业化学和材料化学的合成中应用。该计划不可或缺的一部分是招募和准备多样化的STEM（科学，技术，工程和数学）劳动力，以促进科学领域。该项目通过与一家大型制药公司的合作为学生提供了工业培训的机会。 Ngai教授建立了一个动手合成模块，向高中生引入有机合成和分子光化学和一个夏季工业实习计划，以更好地为研究生为先进化学化学制造业的未来职业做好准备。通常是因为其他对映异构体是无效或有害的。结果，可以容易地增加分子的结构复杂性的同时保持对新形成的立体中心的立体化学的控制在药物发现和发育中至关重要的催化反应。可见光光毒素催化已成为有机合成中潜在强大的工具。 这种催化改变了化学家处理一些困难的合成问题的方式。光催化反应的精确立体控制仍然是一个重大挑战。这项研究的重点是手性刘易斯酸催化剂的设计和开发，该催化剂能够立体选择性，可见光介导的光毒素催化。这些新的催化剂应用于羰基和氨基衍生物与烷烃的对映选择性交叉偶联反应。该项目生成了一个新型三叉戟手性配体和手性催化剂的库，这些配体指导不对称化学转化的发展。 Ngai教授开发的动手有机综合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。这些活动还为服务前化学教师的专业发展提供了培训机会。 Boehringer Ingelheim的一项既定的工业合作和暑期实习计划进一步支持高级化学制造业的职业发展。该奖项反映了NSF的法定任务，并被认为是值得通过基金会的智力优点和更广泛影响的审查标准通过评估来支持的。