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CAREER: Development of Stereoselective Cu-Catalyzed Reductive Coupling Reactions

职业：立体选择性铜催化还原偶联反应的发展

基本信息

批准号：
2143712
负责人：
Joshua Sieber
金额：
$ 60万
依托单位：
Virginia Commonwealth University
依托单位国家：
美国
项目类别：
Continuing Grant
财政年份：
2022
资助国家：
美国
起止时间：
2022-09-01 至 2027-08-31
项目状态：
未结题

来源：
https://www.nsf.gov/awardsearch/showAward?AWD_ID=2143712&HistoricalAwards=false
关键词：
CAREER Development Stereoselective Cu Catalyzed

项目摘要

With the support of the Chemical Catalysis program in the Division of Chemistry, Joshua Sieber of the Department of Chemistry at Virginia Commonwealth University (VCU) will investigate and develop new chemical tools to synthesize amine-derived polar organic compounds. These compounds are prevalent in nature, and the pharmaceutical industry uses and develops them to study biological processes and create new therapeutics for the treatment of human diseases. However, such compounds are often extremely difficult to access and synthesize. The goals of this research are to develop new synthetic tools to enable easy access to these important amine-derived organic compounds using earth-abundant copper metal-based catalyst systems. Studies will also be performed to understand how these processes work so that the efficiency of these new techniques can be continually improved. The educational objective of this CAREER proposal aims to recruit and prepare a diverse STEM (Science, Technology, Engineering and Mathematics) workforce for careers at the frontiers of the chemical sciences through hands-on training of the scientific method using the framework of synthetic organic chemistry. This goal will be achieved through: 1) introducing Richmond Public High School students to careers in synthetic organic chemistry through interactive classroom visits and opportunities to perform scientific research in the principal investigator’s laboratory in the summer, and 2) developing a new undergraduate advanced organic chemistry laboratory at VCU aimed at providing synthesis skills to students for applications to industrial careers in chemistry.Development of synthetic methodology to enable the construction of C–C bonds is at the core of organic chemistry. Having a “toolbox” of C–C bond-forming reactions enables the synthetic chemist to access many molecular organic targets desired for applications in chemical biology, medicinal chemistry and materials science. This proposal aims to develop new stereoselective and regiodivergent Cu-catalyzed processes to introduce multiple heteroatom-groups in the final product in a single reaction step to allow for convenient and straightforward access to chiral poly(heteroatom)-containing compounds. The core of the investigation will consist of the study of allenamides in asymmetric Cu-catalyzed reductive coupling reactions with aldehyde and imine electrophiles. Development of these processes is expected to: 1) improve the synthetic efficiency for the preparation of molecular architectures that are difficult to prepare by other techniques; 2) allow for the conversion of basic feedstocks to a wide range of enantio-enriched chiral building blocks of significance in natural product synthesis, chemical biology and chiral catalyst design, and 3) provide mechanistic insights to aid in the future development of general, stereoselective catalytic umpolung (polarity-reversed) processes.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.

在化学系化学催化项目的支持下，弗吉尼亚联邦大学（VCU）化学系的约书亚·西伯将研究和开发新的化学工具来合成胺衍生的极性有机化合物。这些化合物在自然界中普遍存在，制药行业使用和开发它们来研究生物过程并创造用于治疗人类疾病的新疗法。然而，这些化合物通常极难获得和合成。这项研究的目标是开发新的合成工具，使这些重要的胺衍生的有机化合物使用地球丰富的铜金属为基础的催化剂系统容易获得。还将进行研究，以了解这些过程是如何工作的，以便这些新技术的效率可以不断提高。该职业建议的教育目标旨在通过使用合成有机化学框架的科学方法的实践培训，为化学科学前沿的职业招募和准备多元化的STEM（科学，技术，工程和数学）劳动力。这一目标将通过以下方式实现：1）通过互动式课堂参观和夏季在首席研究员实验室进行科学研究的机会，向里士满公立高中学生介绍合成有机化学的职业生涯，和2）发展一个新的本科生先进的有机化学实验室，旨在提供合成技能，以学生应用到工业职业的化学。发展能够构建C-C键的合成方法是有机化学的核心。拥有C-C键形成反应的“工具箱”使合成化学家能够获得化学生物学，药物化学和材料科学中应用所需的许多分子有机目标。该提议旨在开发新的立体选择性和区域发散性Cu催化方法，以在单个反应步骤中在最终产物中引入多个杂原子基团，从而允许方便和直接地获得手性含多（杂原子）化合物。研究的核心将包括联烯酰胺在铜催化的不对称还原偶联反应与醛和亚胺亲电试剂的研究。这些方法的发展有望：1）提高合成效率，用于制备其他技术难以制备的分子结构; 2）允许碱性原料转化为在天然产物合成、化学生物学和手性催化剂设计中具有重要意义的广泛的对映体富集的手性结构单元，3）提供机械的见解，以帮助在未来发展的一般，立体选择性催化umpolung（极性反转）过程。这个奖项反映了NSF的法定使命，并已被认为是值得支持的，通过评估使用基金会的知识价值和更广泛的影响审查标准。