SusChEM: New Hydrogen Bond Donor Catalysts for Asymmetric Synthesis

SusChEM：用于不对称合成的新型氢键供体催化剂

基本信息

批准号：
1566402
负责人：
Viresh Rawal
金额：
$ 45万
依托单位：
University of Chicago
依托单位国家：
美国
项目类别：
Continuing Grant
财政年份：
2016
资助国家：
美国
起止时间：
2016-06-15 至 2019-05-31
项目状态：
已结题

来源：
https://www.nsf.gov/awardsearch/showAward?AWD_ID=1566402&HistoricalAwards=false
关键词：
SusChEM New Hydrogen Bond Donor

项目摘要

The Chemical Catalysis Program of the Chemistry Division supports the project by Professor Viresh H. Rawal. Professor Rawal is a faculty member in the Department of Chemistry at the University of Chicago. He is investigating the design and use of novel small molecule catalysts that, like enzymes, can activate reactants through hydrogen bond interactions and thereby catalyze highly selective reactions. This metal-free acceleration of reactions is not only of fundamental interest, but also has benefits to society, since metal impurities are undesirable in consumer products, such as specialty materials and medicines. The research focuses on the development of new hydrogen bonding catalysts, including bifunctional catalysts, for the synthesis of chiral substances. Such compounds possess mirror asymmetry and have considerable economic and biomedical importance. These projects provide training in chemical synthesis, problem solving, and oral and written communication to researchers at all levels. Through this work, Professor Rawal provides scientific research opportunities for students from underrepresented groups.New classes of chiral hydrogen bond donor compounds are being developed and examined as catalysts for asymmetric reactions. These novel hydrogen (H)-bond donor scaffolds are expected to expand the classes of reactions that can be rendered enantioselective and lead to improvements in the effectiveness and substrate scope of other reactions. A particular focus is on the study of catalysts possessing two or more H-bond donor groups, enabling the activation of substrates containing a carbonyl group, an important functional group for organic synthesis. The catalysts under study probe the importance of the distance between the two donor hydrogens, as well as their acidity, for effective activation of the carbonyl group. The investigations, which are carried out in conjunction with mechanistic, computational, and crystallographic studies, provide information on the activation capabilities of the new hydrogen bond donor scaffolds. Three distinct catalyst scaffolds are under development. The structural and reactivity properties of each are examined in a wide range of reactions. Studies show that the catalysts are highly active, requiring only 0.1-1 mol% loading, so they provide environmentally friendly solutions for chemical synthesis. The work opens access to a wide range of chiral compounds, of importance for natural product synthesis, drug development, and materials chemistry. Outreach activities involve participation by high-school students, particularly those from underrepresented groups.

化学部化学催化项目支持 Viresh H. Rawal 教授的项目。拉瓦尔教授是芝加哥大学化学系的教员。他正在研究新型小分子催化剂的设计和使用，这些催化剂像酶一样，可以通过氢键相互作用激活反应物，从而催化高选择性反应。这种无金属的反应加速不仅具有根本利益，而且对社会也有好处，因为金属杂质在特种材料和药品等消费品中是不受欢迎的。该研究重点是开发用于合成手性物质的新型氢键催化剂，包括双功能催化剂。此类化合物具有镜像不对称性并且具有相当大的经济和生物医学重要性。这些项目为各级研究人员提供化学合成、问题解决以及口头和书面交流方面的培训。通过这项工作，Rawal 教授为来自代表性不足群体的学生提供了科学研究机会。新型手性氢键供体化合物正在开发和测试，作为不对称反应的催化剂。这些新型氢（H）键供体支架有望扩大可实现对映选择性的反应类别，并改善其他反应的有效性和底物范围。特别关注具有两个或多个氢键供体基团的催化剂的研究，该催化剂能够活化含有羰基的底物，羰基是有机合成的重要官能团。正在研究的催化剂探讨了两个供体氢之间的距离及其酸性对于有效活化羰基的重要性。这些研究与机械、计算和晶体学研究结合进行，提供了有关新型氢键供体支架活化能力的信息。三种不同的催化剂支架正在开发中。每个化合物的结构和反应性质都在广泛的反应中进行了检查。研究表明，该催化剂活性高，仅需0.1-1 mol%的负载量，为化学合成提供了环保的解决方案。这项工作为人们获得了广泛的手性化合物提供了机会，这些化合物对于天然产物合成、药物开发和材料化学具有重要意义。外展活动需要高中生的参与，特别是来自代表性不足群体的高中生的参与。