CAREER: Stereoselective manipulation of unstabilized carbocations

职业：不稳定碳正离子的立体选择性操纵

• 批准号: 1352587
• 负责人: Ryan Shenvi
• 金额: $ 60万
• 依托单位: The Scripps Research Institute
• 依托单位国家: 美国
• 项目类别: Standard Grant
• 财政年份: 2014
• 资助国家: 美国
• 起止时间: 2014-04-01 至 2019-03-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1352587&HistoricalAwards=false
• 关键词: CAREER; Stereoselective; manipulation; unstabilized; carbocations

With this CAREER award, the Chemical Synthesis Program is supporting the research and educational efforts of Dr. Ryan A. Shenvi of the Department of Chemistry at the Scripps Research Institute. The focus of this research is to develop a new class of stereoselective nucleophilic displacement reactions that operate on isolated tertiary carbon centers through attack of unstabilized carbocationic contact ion pairs. This research fills a major methodological gap in chemical synthesis that has been recognized for nearly 100 years. Realization of the goals of this proposal would broadly impact the synthesis of challenging tert-alkyl-substituted chiral materials that are difficult or impossible to access by other methods. A successful outcome of the research proposed here entails the reaction of unstabilized carbocations and various nucleophiles with high chemo- and stereoselectivity, which has important consequences for the production of materials for the interfacing fields of biology, medicine, and physics.The key focus of this research is on the development of concise and scalable syntheses of therapeutically relevant molecules through the invention of new chemical reactions that allow a degree of complexity which has been unachievable through standard methods. The proposed research will potentially allow ready access to a number of important natural and unnatural products while reducing the number of steps and increasing the efficiency. The educational component of this grant involves curriculum development and outreach through the Scripps SURF program. This effort involves the development of a curriculum for high-school, undergraduate, and graduate education that articulates the scientific method in the context of organic chemistry research.

通过此职业奖，化学综合计划正在支持Scripps研究所化学系Ryan A. Shenvi博士的研究和教育工作。 这项研究的重点是开发一类新的立体选择性亲核位移反应，该反应通过未稳定的碳定位接触离子对的攻击在分离的第三级碳中心上运行。这项研究填补了化学合成的主要方法论差异，该差距已被认可了近100年。实现该提案的目标将广泛影响挑战性的Tert烷基取代的手性材料的综合，这些材料难以或无法通过其他方法访问。此处提出的研究的成功结果需要具有高化学和立体选择性的不稳定碳和各种亲核者的反应，这对生产生物学，医学和物理的交互材料的生产具有重要的后果。这项研究的关键重点是通过涉及与概述的合成的相关性的发展，允许使用相关的合成，并具有相关的合成性。通过标准方法无法实现的复杂性。拟议的研究将有可能允许随时可以访问许多重要的天然和不自然产品，同时减少步骤的数量并提高效率。 该赠款的教育部分涉及通过Scripps Surf计划开发课程和宣传。这项工作涉及开发用于高中，本科和研究生教育的课程，该课程在有机化学研究的背景下阐明了科学方法。