New Concepts for Multifunctional Asymmetric Catalysis

多功能不对称催化新概念

• 批准号: 1856613
• 负责人: Daniel Seidel
• 金额: $ 48.5万
• 依托单位: University of Florida
• 依托单位国家: 美国
• 项目类别: Standard Grant
• 财政年份: 2019
• 资助国家: 美国
• 起止时间: 2019-07-01 至 2023-06-30
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1856613&HistoricalAwards=false
• 关键词: New; Concepts; Multifunctional; Asymmetric; Catalysis

With this Award, the Chemical Synthesis Program of the NSF Division of Chemistry supports the research of Professor Daniel Seidel of the Department of Chemistry at the University of Florida. The ability to prepare complex molecules in the most cost-effective way possible is directly dependent on the availability of sustainable synthetic methodologies. The new synthetic methods that emerge from this work may provide novel ways to make biologically important compounds such as polycyclic ethers, amines, and indole containing substances, which should, in turn, help advance the chemical industry, which itself is linked to the US economy. The research provides training for graduate and undergraduate student, preparing them for future careers in industry and academia. Underrepresented minority students are actively recruited to participate. Students working on this project gain expertise in modern synthetic methods and laboratory techniques while being exposed to an intellectually stimulating and challenging environment.This project aims to advance the field of asymmetric catalysis on a fundamental level through exploration of conceptually new and underdeveloped methods of substrate activation. A major goal is the development of reactions that produce enantiomerically enriched products through intervention of chiral ion pairs. Novel Bronsted acids and hydrogen bond donor catalysts are explored to facilitate enantioselective processes and address challenging synthetic problems. A focus is on reactions that proceed via the intermediacy of highly reactive oxocarbenium ions and related species. Multifunctional catalysts are being developed with the goal of achieving enzyme-like catalysis under mild reaction conditions.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.

有了这个奖，化学NSF部门的化学合成计划支持佛罗里达大学化学系的丹尼尔塞德尔教授的研究。 以最具成本效益的方式制备复杂分子的能力直接取决于可持续合成方法的可用性。 从这项工作中出现的新合成方法可能提供新的方法来制造生物重要的化合物，如多环醚，胺和含吲哚的物质，这反过来又有助于推动化学工业，这本身就与美国经济有关。 该研究为研究生和本科生提供培训，为他们未来在工业和学术界的职业生涯做好准备。代表性不足的少数民族学生被积极招募参加。该项目的学生将在现代合成方法和实验室技术方面获得专业知识，同时接触到一个智力刺激和具有挑战性的环境。该项目旨在通过探索概念上新的和欠发达的底物活化方法，在基础水平上推进不对称催化领域。 一个主要的目标是开发通过手性离子对的干预产生对映体富集产物的反应。 新型布朗斯台德酸和氢键供体催化剂的探索，以促进对映选择性的过程，并解决具有挑战性的合成问题。 重点是通过高活性氧碳正离子和相关物种的中间体进行的反应。 多功能催化剂正在开发中，其目标是在温和的反应条件下实现类似酶的催化作用。该奖项反映了NSF的法定使命，通过使用基金会的知识价值和更广泛的影响审查标准进行评估，被认为值得支持。

项目成果

N-Fluorenyltryptamines as a Useful Platform for Catalytic Enantio­selective Pictet–Spengler Reactions

N-芴基色胺作为催化对映选择性 Pictet-Spengler 反应的有用平台

• DOI: 10.1055/a-1970-4452
• 发表时间: 2023
• 期刊: Synthesis
• 作者: Adili, Alafate;Sole, Aniket V.;Das, Bishwaprava;Matter, Megan E.;Seidel, Daniel
• 通讯作者: Seidel, Daniel

Catalytic Enantioselective Approaches to the oxa-Pictet–Spengler Cyclization and Other 3,6-Dihydropyran-Forming Reactions

氧杂皮克泰·斯宾格勒环化和其他 3,6-二氢吡喃形成反应的催化对映选择性方法

• DOI: 10.1055/s-0039-1690686
• 发表时间: 2019
• 期刊: SynOpen
• 影响因子: 2.5
• 作者: Zhu, Zhengbo;Adili, Alafate;Zhao, Chenfei;Seidel, Daniel
• 通讯作者: Seidel, Daniel

A Selenourea-Thiourea Brønsted Acid Catalyst Facilitates Asymmetric Conjugate Additions of Amines to α,β-Unsaturated Esters.

• DOI: 10.1021/jacs.9b12457
• 发表时间: 2020-03-25
• 期刊: Journal of the American Chemical Society
• 影响因子: 15
• 作者: Lin Y;Hirschi WJ;Kunadia A;Paul A;Ghiviriga I;Abboud KA;Karugu RW;Vetticatt MJ;Hirschi JS;Seidel D
• 通讯作者: Seidel D

Highly Acidic Conjugate‐Base‐Stabilized Carboxylic Acids Catalyze Enantioselective oxa‐Pictet–Spengler Reactions with Ketals

高酸性缀合物 - 碱 - 稳定的羧酸催化对映选择性氧杂 - Pictet - 与缩酮的 Spengler 反应

• DOI: 10.1002/ange.201912677
• 发表时间: 2019
• 期刊: Angewandte Chemie
• 作者: Zhu, Zhengbo;Odagi, Minami;Zhao, Chenfei;Abboud, Khalil A.;Kirm, Helmi Ulrika;Saame, Jaan;Lõkov, Märt;Leito, Ivo;Seidel, Daniel
• 通讯作者: Seidel, Daniel