CAREER: Stereochemically-Flexible Polyol Synthesis

职业：立体化学柔性多元醇合成

• 批准号: 1453896
• 负责人: Jason Chen
• 金额: $ 65万
• 依托单位: Iowa State University
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 2015
• 资助国家: 美国
• 起止时间: 2015-07-01 至 2017-06-30
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1453896&HistoricalAwards=false
• 关键词: CAREER; Stereochemically; Flexible; Polyol; Synthesis

In this project jointly funded by the Chemical Synthesis program of the Chemistry Division and the Experimental Program to Stimulate Competitive Research (EPSCoR), Professor Jason Chen of Iowa State University is developing methods to prepare complex polyoxygenated molecules. Educational modules in development by Professor Chen introduce local high school students to the importance of organic chemistry in modern medicine. The broader impacts of this work include potential advances in synthetic organic chemistry from the discovery of new methods to install dense arrays of oxygen-containing stereocenters and the encouragement of high school students to pursue STEM careers.The methods emphasize tunable control over the placement of the oxygen atoms and the ability to introduce multiple oxygen atoms at the same time. This project focuses on setting multiple contiguous alcohol chiral centers with flexible stereochemistry. The key reactions are enantioselective, organocatalytic, polyoxygenation of enals and nucleophilic addition to alpha-oxygenated aldehydes. These reactions complement each other and can potentially deliver up to five contiguous stereocenters in two steps. The polyoxygenated structures prepared by these methods are commonly found in molecules with useful biological properties.

在这个由化学部化学合成计划和刺激竞争研究实验计划（EPSCoR）共同资助的项目中，爱荷华州州立大学的Jason Chen教授正在开发制备复杂多氧分子的方法。陈教授正在开发的教育模块向当地高中生介绍有机化学在现代医学中的重要性。这项工作的更广泛影响包括合成有机化学的潜在进步，包括发现安装含氧立体中心密集阵列的新方法，以及鼓励高中生从事STEM职业。这些方法强调对氧原子位置的可调控制，以及同时引入多个氧原子的能力。本项目的重点是设置多个连续的醇手性中心与灵活的立体化学。关键的反应是对映选择性、有机催化、烯醛的多加氧和与α-含氧醛的亲核加成反应。这些反应相互补充，并且可以在两个步骤中潜在地递送多达五个连续的立体中心。通过这些方法制备的多氧结构通常存在于具有有用生物学性质的分子中。