CAREER: New Catalysts and Methods for Amine Synthesis via Stereoselective Allene Aziridination

职业：通过立体选择性丙二烯氮丙啶化合成胺的新催化剂和方法

• 批准号: 1254397
• 负责人: Jennifer Schomaker
• 金额: $ 55万
• 依托单位: University of Wisconsin-Madison
• 依托单位国家: 美国
• 项目类别: Standard Grant
• 财政年份: 2013
• 资助国家: 美国
• 起止时间: 2013-07-01 至 2018-06-30
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1254397&HistoricalAwards=false
• 关键词: CAREER; New; Catalysts; Methods; Amine

With this CAREER Award, the Chemistry Division's Synthesis and Catalysis programs are supporting the research of Professor Jennifer M. Schomaker of the University of Wisconsin-Madison. Professor Schomaker will develop new allene oxidation methodologies to permit the rapid and flexible syntheses of complex, enantioenriched and densely functionalized amine motifs that are important components of natural products, ligands for catalysis and probes of biological processes. The first goal of this project is to develop reliable methods for regio- and stereocontrolled allene aziridination to reactive bicyclic methylene aziridine scaffolds. Second, methods to transform these key intermediates into aminated stereotriads (compounds containing three consecutive heteroatom-bearing chiral carbons) will be developed, providing access to a diverse array of nitrogen-containing building blocks for synthesis. Finally, the third goal of this project is to apply allene aziridination to the synthesis of jogyamycin, a complex aminocyclopentitol exhibiting potent antibiotic, antitumor, antiprotozoal and antimalarial activities. The need for increasingly chemo- and stereoselective catalysis presents exciting challenges for the development of new synthetic organic methodologies. Schomaker's work will identify new paradigms in catalysis for the chemoselective construction of carbon-nitrogen bonds. These new modes of catalysis will enable powerful approaches to the synthesis of biologically relevant molecules. The broader impacts of her work will be realized through collaboration with the PEOPLE program (Pre-College Enrichment Opportunity Program for Learning Excellence) at UW-Madison. She will identify economically disadvantaged local students early in their high school careers and provide mentored opportunities for research experiences focusing on the development of new synthetic methodologies. Students will have ample time to develop valuable laboratory skills, learn to communicate scientifically in both oral and written forms and participate in seminars to broaden their understanding of the role research plays in addressing important societal concerns. Students will also employ social media to track their progress and share their experiences with family, friends and classmates.

有了这个职业奖，化学部的合成和催化方案是支持教授詹妮弗M。威斯康星大学麦迪逊分校的Schomaker。 Schomaker教授将开发新的丙二烯氧化方法，以快速灵活地合成复杂的，对映体富集的和密集功能化的胺基序，这些胺基序是天然产物，催化配体和生物过程探针的重要组成部分。 本项目的第一个目标是开发可靠的方法，用于区域和立体控制的丙二烯氮丙啶反应活性双环亚甲基氮丙啶支架。 第二，将开发将这些关键中间体转化为胺化立体三单元（含有三个连续的含杂原子手性碳的化合物）的方法，从而提供多种含氮结构单元的合成途径。 最后，本项目的第三个目标是将丙二烯氮丙啶化应用于乔吉霉素的合成，乔吉霉素是一种具有强效抗生素、抗肿瘤、抗原生动物和抗疟疾活性的复合物氨基环戊糖醇。对化学和立体选择性催化的需求日益增加，这对新的有机合成方法的发展提出了令人兴奋的挑战。 Schomaker的工作将为碳-氮键的化学选择性结构的催化确定新的范例。这些新的催化模式将使生物相关分子的合成成为可能。 她的工作的更广泛的影响将通过与人的程序（大学前丰富的学习机会计划卓越）在威斯康星大学麦迪逊分校的合作实现。她将确定经济上处于不利地位的当地学生在他们的高中生涯的早期，并提供指导的机会，研究经验，重点是新的合成方法的发展。学生将有充足的时间来发展宝贵的实验室技能，学习以口头和书面形式进行科学交流，并参加研讨会，以扩大他们对研究在解决重要社会问题中所起作用的理解。 学生还将使用社交媒体来跟踪他们的进步，并与家人，朋友和同学分享他们的经验。