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:
  • 金额:
    $ 45万
  • 依托单位:
  • 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

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.
化学部的化学催化计划支持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,这种催化剂像酶一样,可以通过氢键相互作用激活反应物,从而催化高选择性的反应。这种无金属加速反应不仅具有根本利益,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。本研究的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。这类化合物具有镜像不对称性,具有重要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,拉瓦尔教授为来自代表不足的基团的学生提供了科学研究的机会。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。这些新型的氢键供体支架有望扩大反应的类别,使反应具有对映选择性,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供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。正在研究的催化剂探索了两个给体氢原子之间的距离以及它们的酸度对于有效激活羰基的重要性。这些研究与机械、计算和结晶学研究相结合,提供了关于新的氢键给体支架的激活能力的信息。三种不同的催化剂支架正在开发中。在广泛的反应中考察了每种化合物的结构和反应性。研究表明,该催化剂具有很高的活性,只需要0.1-1%的负载量,为化学合成提供了环境友好的解决方案。这项工作打开了获得广泛的手性化合物的途径,这些化合物对天然产物合成、药物开发和材料化学具有重要意义。外联活动涉及高中生的参与,特别是来自代表人数不足的群体的学生。

项目成果

期刊论文数量(5)
专著数量(0)
科研奖励数量(0)
会议论文数量(0)
专利数量(0)
Synthesis of 1,2-Oxazinanes via Hydrogen Bond Mediated [3 + 3] Cycloaddition Reactions of Oxyallyl Cations with Nitrones
氢键介导的 1,2-恶嗪烷合成 [3 3] 草烯丙基阳离子与硝酮的环加成反应
  • DOI:
    10.1021/acs.orglett.8b02301
  • 发表时间:
    2018
  • 期刊:
  • 影响因子:
    5.2
  • 作者:
    Rombola, M.;Rawal, V.H.
  • 通讯作者:
    Rawal, V.H.
Total Synthesis of (−)-Ambiguine P
()-Ambiguine P 的全合成
Dicyclopentyl Dithiosquarate as an Intermediate for the Synthesis of Thiosquaramides
  • DOI:
    10.1021/acs.orglett.7b03549
  • 发表时间:
    2018-02-02
  • 期刊:
  • 影响因子:
    5.2
  • 作者:
    Rombola, Michael;Rawal, Viresh H.
  • 通讯作者:
    Rawal, Viresh H.
Development of Chiral, Bifunctional Thiosquaramides: Enantioselective Michael Additions of Barbituric Acids to Nitroalkenes
  • DOI:
    10.1021/jacs.7b01115
  • 发表时间:
    2017-04-19
  • 期刊:
  • 影响因子:
    15
  • 作者:
    Rombola, Michael;Sumaria, Chintan S.;Rawal, Viresh H.
  • 通讯作者:
    Rawal, Viresh H.
Rapid construction of tetrahydropyridine scaffolds via formal imino Diels–Alder reactions of Schiff bases and Nazarov reagents
通过席夫碱和纳扎罗夫试剂的正式亚氨基狄尔斯-阿尔德反应快速构建四氢吡啶支架
  • DOI:
    10.1039/c9ob01880h
  • 发表时间:
    2019
  • 期刊:
  • 影响因子:
    0
  • 作者:
    Wu, Y. -K.;Rawal, V. H.
  • 通讯作者:
    Rawal, V. H.
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Viresh Rawal其他文献

Viresh Rawal的其他文献

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{{ truncateString('Viresh Rawal', 18)}}的其他基金

Methods for the Chemical Synthesis of Complex Molecules
复杂分子的化学合成方法
  • 批准号:
    1900594
  • 财政年份:
    2019
  • 资助金额:
    $ 45万
  • 项目类别:
    Standard Grant
Workshop Series on Organic Synthesis and Natural Products Chemistry (2007)
有机合成和天然产物化学研讨会系列(2007)
  • 批准号:
    0740105
  • 财政年份:
    2007
  • 资助金额:
    $ 45万
  • 项目类别:
    Standard Grant
Catalytic Methods for Asymmetric Synthesis
不对称合成的催化方法
  • 批准号:
    0316803
  • 财政年份:
    2003
  • 资助金额:
    $ 45万
  • 项目类别:
    Continuing Grant

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