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New Cycloaddition and Annulation Strategies for Organic Synthesis

有机合成的新环加成和成环策略

基本信息

批准号：
1900391
负责人：
Rick Danheiser
金额：
$ 48.5万
依托单位：
Massachusetts Institute of Technology
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：
2019-08-01 至 2022-07-31
项目状态：
已结题

来源：
https://www.nsf.gov/awardsearch/showAward?AWD_ID=1900391&HistoricalAwards=false
关键词：
New Cycloaddition Annulation Strategies Organic

项目摘要

With this award, the Chemical Synthesis Program of the Division of Chemistry is supporting the research of Professor Rick L. Danheiser of the Department of Chemistry at the Massachusetts Institute of Technology. In this research program, Professor Danheiser and his students are developing new methods for the chemical synthesis of cyclic organic molecules that are incorporated in the chemical structures of numerous biologically-important compounds. The development of highly efficient methods for the synthesis of these molecules has great value in providing improved access to compounds with important applications in medicine, materials chemistry, agriculture and electronics. The goal of this research program is the development of new synthetic strategies with the power to dramatically streamline the synthesis of these classes of compounds. The utility of these new methods is being demonstrated by their application to the synthesis of several naturally-occurring compounds that have activity as antitumor agents, but which are not available in large quantities from their sources in nature. The graduate students supported under this grant serve as coordinators for the MIT Outreach Program, which each year visits about 25 high schools in the New England region providing presentations on chemistry and careers in science. Approximately 1,200-1,500 high school students attend these presentations each year, with up to 50% of the students being members of underrepresented minority groups. Dr. Danheiser is also a recognized leader in chemical safety.This research advances the ability of chemists to develop efficient syntheses of several important classes of organic compounds including polycyclic aromatic molecules and heterocyclic systems such as indoles and pyridines. The methods under investigation involve mechanistically novel transformations. These studies are furthering the understanding of the chemistry of unusual reactive species such as strained cyclic allenes and alkynes, vinylketenes, vinylallenes, and several other classes of highly unsaturated conjugated molecules. From the perspective of sustainability, the methodology under development has several attractive features. Most of the methods are highly atom economical, i.e., all of the atoms of the reactants are incorporated in the products, minimizing the generation of chemical waste. In addition, most of the new cycloadditions are triggered simply by heat or light, avoiding the need for even catalytic amounts of reagents (especially heavy metal catalysts). Synthesis is often described as the "enabling technology" of chemistry. The synthetic methods provide researchers in both academia and industry with new tools to design and make heterocyclic compounds with applications in medicine, agriculture, electronics, and other areas. The graduate students supported under this program receive training to develop their skills as synthetic chemists, in scientific ethics, and in developing their oral and written communication skills.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.

有了这个奖项，化学系的化学合成计划支持教授里克L。马萨诸塞州理工学院化学系的丹海瑟。在这个研究项目中，Danheiser教授和他的学生正在开发用于化学合成环状有机分子的新方法，这些分子被纳入许多生物重要化合物的化学结构中。开发用于合成这些分子的高效方法在提供改善获得在医学、材料化学、农业和电子学中具有重要应用的化合物方面具有巨大价值。该研究计划的目标是开发新的合成策略，以显着简化这些化合物的合成。这些新方法的实用性通过它们在合成几种天然存在的化合物中的应用而得到证明，这些化合物具有作为抗肿瘤剂的活性，但它们在自然界中不能从它们的来源大量获得。该补助金支持的研究生担任麻省理工学院外展计划的协调员，该计划每年访问新英格兰地区约25所高中，提供有关化学和科学职业的演讲。每年大约有1，200 - 1，500名高中生参加这些演讲，其中多达50%的学生是代表性不足的少数群体成员。 Danheiser博士也是化学安全领域公认的领导者。该研究提高了化学家开发几类重要有机化合物的有效合成的能力，包括多环芳香分子和杂环系统，如吲哚和吡啶。正在调查的方法涉及机械新颖的转换。这些研究正在进一步了解不寻常的反应物种的化学，如应变环状联烯和炔，乙烯基烯酮，乙烯基联烯，和其他几类高度不饱和的共轭分子。从可持续性的角度来看，正在制定的方法有几个有吸引力的特点。大多数方法是高度原子经济的，即，反应物的所有原子都结合在产物中，从而使化学废物的产生最小化。此外，大多数新的环加成反应仅通过热或光引发，避免了甚至催化量的试剂（特别是重金属催化剂）的需要。合成通常被描述为化学的“使能技术”。这些合成方法为学术界和工业界的研究人员提供了新的工具来设计和制造杂环化合物，并在医学，农业，电子和其他领域应用。该计划资助的研究生接受培训，以发展他们作为合成化学家的技能，科学伦理，以及发展他们的口头和书面沟通技能。该奖项反映了NSF的法定使命，并通过使用基金会的智力价值和更广泛的影响审查标准进行评估，被认为值得支持。