NSF Career: Enamine-Metal Lewis Acid Bifunctional Catalysts for Asymmetric Organic Transformations

NSF 职业：用于不对称有机转化的烯胺-金属路易斯酸双功能催化剂

• 批准号: 1056420
• 负责人: Hong Wang
• 金额: $ 54.99万
• 依托单位: Miami University
• 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: 2011-03-01 至 2016-11-30
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1056420&HistoricalAwards=false
• 关键词: NSF; Career; Enamine; Metal; Lewis

Professor Hong Wang of Miami University Oxford Campus is supported by the Chemical Catalysis (CAT) Program in the Division of Chemistry to develop bifunctional catalysts combining a metal center with an organocatalytic center on a single molecule for potential applications in asymmetric organic transformations. Bifunctional enamine-metal Lewis acid catalysts will be synthesized and used for asymmetric carbon-carbon and carbon-heteroatom bond forming reactions which cannot be achieved without the synergistic action of the two catalytic centers. Direct aldol condensations with ketones and inverse-electron-demand hetero-Diels-Alder reactions will be investigated. The catalyst design allows for the combination of different amine bases with different metals, which broadens the spectrum of applicability of these bifunctional catalytic systems to a wide range of organic reactions. The development of Lewis acid-Lewis base bifunctional systems is challenging because the acid and the base are prone to self-quenching and inactivation. The proposed research promises to circumvent this problem by judicious molecular architecture with sufficient flexibility to bring the organic base and the metal Lewis acid into close proximity but with enough rigidity and steric hindrance to prevent their binding. The proposed research could significantly impact asymmetric catalysis and the synthesis of fine chemicals and pharmaceuticals. The results will be integrated into a new graduate course in catalysis and an outreach plan will be implemented to provide summer research experience to minority undergraduate students and their teachers from Texas A&M University-Kingsville and to high school teachers from area high schools.

迈阿密大学牛津校园的洪王教授得到了化学催化（CAT）化学部计划的支持，以开发双功能催化剂，该催化剂将金属中心与单个分子上的有机催化中心相结合，以用于非对称有机转化的潜在应用。双功能的磁胺 - 金属刘易斯酸催化剂将被合成并用于不对称的碳碳和碳原子质键形成反应，如果没有两个催化中心的协同作用，这些反应将无法实现。将研究与酮的直接醛醇缩合和逆电子杂音杂音 - 抗二烷 - alder反应。催化剂设计允许将不同的胺碱与不同的金属组合在一起，从而将这些双功能催化系统的适用性扩大到广泛的有机反应。刘易斯酸刘易斯基碱双功能系统的发展是具有挑战性的，因为酸和碱很容易自我淬火和灭活。拟议的研究有望通过具有足够灵活性的明智分子结构来解决这个问题，以使有机碱和金属刘易斯酸离接近，但具有足够的刚度和空间的阻碍，以防止其结合。拟议的研究可能会显着影响不对称的催化和精细化学物质和药物的合成。结果将纳入催化新的新研究生课程，并将实施一项外展计划，以向来自德克萨斯州A＆M大学 - 金斯维尔的少数族裔本科生及其老师以及来自地区高中的高中老师提供夏季研究经验。