New Methods for Construction of Enantiomerically Enriched Tertiary Alcohols via Nucleophilic Reactions of Enediolates

通过烯二醇酯亲核反应构建对映体富集叔醇的新方法

• 批准号: 1111218
• 负责人: John Wolfe
• 金额: $ 39.5万
• 依托单位: Regents of the University of Michigan - Ann Arbor
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 2011
• 资助国家: 美国
• 起止时间: 2011-09-15 至 2015-08-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1111218&HistoricalAwards=false
• 关键词: New; Methods; Construction; Enantiomerically; Enriched

Professor John P. Wolfe of the University of Michigan is supported by the Chemical Synthesis Program in the Division of Chemistry to carry out research on the development of new chemical reactions for the stereocontrolled assembly of tertiary alpha-hydroxy esters. These functional groups are found in many biologically active molecules as well as important building blocks for complex molecule synthesis. The research is focused on the invention of new techniques to generate reactive enediolates and the investigation of new nucleophilic reactions of enediolates for the preparation of molecules that contain 1-2 quaternary stereocenters. In addition, the research is also directed towards the utilization of new carbon-carbon bond-forming reactions between nucleophilic enediolates and carbon-centered electrophiles for the synthesis of complex carbocyclic and heterocyclic molecules. These new reactions will provide access to valuable organic compounds that cannot easily be prepared in a stereocontrolled fashion with existing methods. The development of new reactions allows chemists to shorten synthetic sequences, saving time, money, and natural resources. This ultimately benefits society by providing important chemicals such as pharmaceuticals at an affordable cost and in an environmentally friendly manner. This research will lead to streamlined routes to compounds with known utility, and will also give access to new compounds that cannot be easily prepared with existing methods. This will afford many opportunities for the discovery of new, useful molecules with applications in fields such as pharmaceuticals, agrochemicals, or materials. The research described above will also provide excellent training to both graduate and undergraduate students, who will master concepts and skills in organic synthesis and synthetic methods development. Upon completion of their training, these students will be well positioned to enter the workforce as productive scientists in industrial, government, or academic laboratories.

密歇根大学John P. Wolfe教授在化学系化学合成项目的支持下，开展了叔α-羟基酯立体控制组装新化学反应的开发研究。这些官能团存在于许多生物活性分子中，也是复杂分子合成的重要组成部分。该研究的重点是发明生成反应性烯二醇酯的新技术，以及研究烯二醇酯的新亲核反应以制备含有1-2个四元立构中心的分子。此外，该研究还致力于利用亲核烯二醇和碳中心亲电子试剂之间的新碳-碳键形成反应来合成复杂的碳环和杂环分子。这些新反应将提供有价值的有机化合物，而这些化合物无法通过现有方法以立体控制的方式轻松制备。新反应的开发使化学家能够缩短合成序列，从而节省时间、金钱和自然资源。通过以可承受的成本和环境友好的方式提供重要的化学品（例如药品），最终使社会受益。这项研究将为具有已知效用的化合物提供简化的路线，并且还将提供使用现有方法无法轻松制备的新化合物。这将为发现新的、有用的分子及其在药物、农用化学品或材料等领域的应用提供许多机会。上述研究还将为研究生和本科生提供良好的培训，使他们掌握有机合成和合成方法开发的概念和技能。完成培训后，这些学生将能够很好地进入劳动力市场，成为工业、政府或学术实验室的高效科学家。