New Concepts for Multifunctional Asymmetric Catalysis

多功能不对称催化新概念

• 批准号: 2154292
• 负责人: Daniel Seidel
• 金额: $ 52.5万
• 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: 2022
• 资助国家: 美国
• 起止时间: 2022-07-01 至 2025-06-30
• 项目状态: 未结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=2154292&HistoricalAwards=false
• 关键词: New; Concepts; Multifunctional; Asymmetric; Catalysis

With the support of the Chemical Synthesis (SYN) program in the Division of Chemistry, Professor Daniel Seidel of the Department of Chemistry at the University of Florida is studying new methods for asymmetric catalysis, particularly in the important area of chiral Brønsted acid catalysis. The ability to prepare complex chiral molecules in the most cost-effective way possible is directly dependent on the availability of sustainable synthetic methodologies. The new synthetic methods being explored and developed in this work have the potential to provide improved access to important compounds such as polycyclic ethers and lactams, with potential applications in the chemical and pharmaceutical industries, as well as throughout academia. Furthermore, this project provides an ideal training ground to prepare the next generation of researchers in the chemical sciences. Undergraduate students from different institutions will participate in the planned activities.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 Brønsted acids and hydrogen bond donor catalysts will be explored to facilitate unprecedented enantioselective processes and address challenging synthetic problems. There is real room for innovation in this area as most such chiral Brønsted acid catalysts studied heretofore are based upon now familiar BINOL-phosphate frameworks. 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 achieveing enzyme-like catalysis and enantioselectivity 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.

在化学系化学合成（SYN）项目的支持下，佛罗里达大学化学系的丹尼尔·塞德尔教授正在研究不对称催化的新方法，特别是在手性布朗斯特酸催化的重要领域。 以最具成本效益的方式制备复杂手性分子的能力直接取决于可持续合成方法的可用性。 在这项工作中探索和开发的新合成方法有可能改善获得多环醚和内酰胺等重要化合物的途径，在化学和制药工业以及整个学术界都有潜在的应用。 此外，该项目为培养下一代化学科学研究人员提供了理想的培训基地。 来自不同院校的本科生将参加计划中的活动。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。 新型布朗斯特酸和氢键供体催化剂将被探索，以促进前所未有的对映选择性过程和解决具有挑战性的合成问题。 在这一领域有真实的创新空间，因为迄今为止研究的大多数手性布朗斯台德酸催化剂是基于现在熟悉的BINOL-磷酸盐框架。 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酶样催化和对映选择性。该奖项反映了NSF的法定使命，并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