SusChEM: New Hydrogen Bond Donor Catalysts for Asymmetric Synthesis

化学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一名教员。他正在研究新型小分子催化剂的设计和使用，像酶一样，可以通过氢键相互作用激活反应物，从而催化高度选择性的反应。这种不含金属的加速反应不仅具有根本的利益，而且对社会也有好处，因为金属杂质在消费品中是不受欢迎的，如特种材料和药品。研究重点是开发新型氢键催化剂，包括双功能催化剂，用于手性物质的合成。这种化合物具有镜像不对称性，具有相当大的经济和生物医学意义。这些项目为各级研究人员提供化学合成、解决问题以及口头和书面交流方面的培训。通过这项工作，Rawal教授为弱势群体的学生提供了科学研究的机会。一类新的手性氢键给体化合物正在被开发和研究作为不对称反应的催化剂。这些新型的氢(H)键供体支架有望扩大可呈现对映选择性的反应类别，并导致其他反应的有效性和底物范围的改善。特别关注的是具有两个或两个以上氢键给体基团的催化剂的研究，这些催化剂能够激活含有羰基的底物，羰基是有机合成的重要官能团。所研究的催化剂探讨了两个给氢之间的距离以及它们的酸度对羰基有效活化的重要性。该研究与机械、计算和晶体学研究相结合，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。每一种的结构和反应性质都在广泛的反应中进行了检验。研究表明，催化剂具有很高的活性，只需要0.1-1 mol%的负载，因此为化学合成提供了环保的解决方案。这项工作为广泛的手性化合物开辟了途径，对天然产物合成、药物开发和材料化学具有重要意义。外联活动需要高中学生，特别是来自代表性不足群体的学生的参与。

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.