Diastereodivergent Catalysis with Modularly Designed Organocatalysts

模块化设计的有机催化剂的非对映发散催化

• 批准号: 1664278
• 负责人: John Zhao
• 金额: $ 45万
• 依托单位: University of Texas at San Antonio
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 2017
• 资助国家: 美国
• 起止时间: 2017-07-01 至 2022-06-30
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1664278&HistoricalAwards=false
• 关键词: Diastereodivergent; Catalysis; Modularly; Designed; Organocatalysts

The Chemical Catalysis Program of the Chemistry Division supports the project by Professor John Zhao. Professor Zhao is a faculty member in the Department of Chemistry at the University of Texas at San Antonio (UTSA). He is developing a new method for the selective synthesis of multiple stereoisomers of organic molecules. Stereoisomers, which differ only subtly in their structures, may have totally different biological and/or pharmacological properties. The goal of this research project is to exploit the unique properties of modularly designed organocatalysts (MDOs) to achieve the easy synthesis of multiple diastereomers of complex organic molecules from the same starting materials, which is presently a very challenging task in chemistry. The research greatly facilitates the exploration of new chemical space and drug discovery. This project offers research opportunities for students, including students from underrepresented minorities, who are preparing for careers in the chemical sciences. UTSA is one of the most diverse institutions of higher education in the United States. Professor Zhao's group provides a high level of education and training for students through a variety of outreach programs that are already in place at UTSA.Catalytic asymmetric syntheses of multiple diastereomers of various important polysubstituted carbocyclic and heterocyclic compounds are under investigation. The researchers use the same starting materials and different modularly designed organocatalysts to selectively generate different stereoisomers of the targets. Specifically, Professor Zhao is pursuing the development of novel MDO catalysts that are self-assembled from readily available precatalysts and the utilization of the MDOs in the catalytic tandem reactions for the diastereodivergent synthesis of polysubstituted carbocyclic and heterocyclic compounds. The method is being investigated for the diastereodivergent syntheses of bioactive natural products of medicinal relevance. The research provides new catalysts that not only achieve the divergent synthesis of different stereoisomers of important molecules, but also improves the stereoselectivity in the synthesis. Stereoselective synthesis is a current challenge in asymmetric catalysis. The research results are being incorporated into an organic laboratory aimed at undergraduates to help stimulate their interest and attract these students to the chemical sciences.

化学系的化学催化项目支持John Zhao教授的项目。赵教授是德克萨斯大学圣安东尼奥分校化学系的教员。 他正在开发一种选择性合成有机分子多种立体异构体的新方法。 立体异构体的结构只有细微差别，但可能具有完全不同的生物学和/或药理学特性。该研究项目的目标是利用模块化设计的有机催化剂（MDO）的独特性质，从相同的起始原料中轻松合成复杂有机分子的多种非对映异构体，这是目前化学中非常具有挑战性的任务。该研究极大地促进了新化学空间的探索和药物发现。该项目为学生提供研究机会，包括来自代表性不足的少数民族的学生，他们正在为化学科学的职业生涯做准备。UTSA是美国最多样化的高等教育机构之一。赵教授的研究小组通过已经在UTSA开展的各种推广项目为学生提供高水平的教育和培训。各种重要的多取代碳环和杂环化合物的多种非对映异构体的催化不对称合成正在研究中。 研究人员使用相同的起始材料和不同的模块化设计的有机催化剂来选择性地产生目标的不同立体异构体。具体而言，赵教授正在开发新型MDO催化剂，这些催化剂是从容易获得的预催化剂中自组装的，并利用MDO在催化串联反应中用于多取代碳环和杂环化合物的非对映异构体合成。该方法正在研究的非对映异构体合成的生物活性天然产品的药用相关性。该研究为实现重要分子不同立体异构体的发散合成提供了新的催化剂，并提高了合成中的立体选择性。 立体选择性合成是当前不对称催化领域的一个挑战。研究结果正在纳入一个针对本科生的有机实验室，以帮助激发他们的兴趣，吸引这些学生对化学科学的兴趣。

项目成果

Domino Michael/Michael reaction catalyzed by switchable modularly designed organocatalysts

可切换模块化设计的有机催化剂催化多米诺迈克尔/迈克尔反应

• DOI: 10.1039/d1ob01991k
• 发表时间: 2021
• 期刊: Organic & Biomolecular Chemistry
• 影响因子: 3.2
• 作者: Parella, Ramarao;Jakkampudi, Satish;Bora, Pranjal;Sakkani, Nagaraju;Zhao, John C.-G.
• 通讯作者: Zhao, John C.-G.

Stereoselective synthesis of chromane derivatives via a domino reaction catalyzed by modularly designed organocatalysts

• DOI: 10.1039/c8ob02677g
• 发表时间: 2019-01-07
• 期刊: ORGANIC & BIOMOLECULAR CHEMISTRY
• 影响因子: 3.2
• 作者: Jakkampudi, Satish;Parella, Ramarao;Zhao, John C. -G.
• 通讯作者: Zhao, John C. -G.

Diastereodivergent Synthesis of Bridged Tetrahydroisoquinoline Derivatives Catalyzed by Modularly Designed Organocatalysts

• DOI: 10.1002/adsc.202000227
• 发表时间: 2020-04-23
• 期刊: ADVANCED SYNTHESIS & CATALYSIS
• 影响因子: 5.4
• 作者: Jakkampudi, Satish;Konda, Swapna;Zhao, John C. -G.
• 通讯作者: Zhao, John C. -G.

Visible light-assisted organocatalytic α-acyloxylation of ketones using carboxylic acids and N-halosuccinimides

使用羧酸和 N-卤代琥珀酰亚胺对酮进行可见光辅助有机催化 α-酰氧基化

• DOI: 10.1039/d2cc04016f
• 发表时间: 2022
• 期刊: Chemical communications
• 影响因子: 4.9
• 作者: Sakkani, Nagaraju;Jha, Dhiraj K.;Whatley, Emily;Zhao, John C.-G.
• 通讯作者: Zhao, John C.-G.

Organocatalytic synthesis of β-enaminyl radicals as the single-electron donors for phenyliodine(III) dicarboxylates: Direct one-pot alkylation-aminoxidation of styrenes

有机催化合成β-烯氨基自由基作为苯碘(III)二羧酸盐的单电子供体：苯乙烯的直接一锅烷基化-氨氧化

• DOI: 10.1039/d2ob01826h
• 发表时间: 2023
• 期刊: Organic & Biomolecular Chemistry
• 影响因子: 3.2
• 作者: Sakkani, Nagaraju;Jha, Dhiraj Kumar;Sadiq, Nouraan;Zhao, John C.-G.
• 通讯作者: Zhao, John C.-G.