Asymmetric Synthesis via Organoboron Compounds

有机硼化合物的不对称合成

• 批准号: 10656577
• 负责人: Ming Chen
• 金额: $ 27.67万
• 依托单位: AUBURN UNIVERSITY AT AUBURN
• 依托单位国家: 美国
• 财政年份: 2022
• 资助国家: 美国
• 起止时间: 2022-07-01 至 2023-08-31
• 项目状态: 已结题
• 来源: https://reporter.nih.gov/project-details/10656577
• 关键词: Address; Agrochemicals; Anions; Area; Biology; Boron; Carbon; Chemicals; Collaborations; Development; Drug Industry; Generations; Health; Human; Methods; Organic Synthesis; Pharmaceutical Chemistry; Process; Property; Reaction; Research; chiral molecule; computational chemistry; design; drug discovery; innovation; materials science; metal complex; novel; programs; three dimensional structure

Project Summary Chiral, nonracemic molecules are highly important in the areas of organic synthesis, material science and chemical biology. They are also of great value to agrochemical and pharmaceutical industries because the three-dimensional structures of chiral molecules allow for the access to broader chemical space in drug discovery. Therefore, the development of catalytic methods that enable the generation of chiral molecules with high enantiopurity is important not only to academic research, but also to pharmaceutical industries, and to human health. Organoboron compounds are useful building blocks in organic synthesis. The boryl group is amenable to a variety of stereospecific chemical transformations. More importantly, the vacant p- orbital of the boron atom can stabilize an anion or a radical in the neighboring carbon atom. This unique property has facilitated the emergence of many innovative catalytic processes to generate enantioenriched organoboronates. In this regards, our group has established a research program centered on asymmetric synthesis using organoboron compounds. We particularly aim to address the challenges in enantioselective synthesis of chiral molecules that are difficult to access by conventional methods. In this proposal, we seek to develop catalytic asymmetric transformations using organoboron compounds by exploiting the novel reactivities of α-boryl metal complexes and α-boryl radicals. Through our continued collaboration with experts in computational chemistry, we will further our understanding of the reaction mechanisms, which will guide us in the direction of transformative reaction design. Meanwhile, the studies will allow for the access to enantioenriched molecules that are valuable for organic synthesis and relevant to drug discovery.

项目摘要 手性、非外消旋分子在有机合成、材料 科学和化学生物学。它们对农用化学品和制药也有很大的价值。 工业，因为手性分子的三维结构允许访问 药物发现中更广阔的化学空间。因此，催化方法的发展 能够产生具有高对映体纯度的手性分子不仅对学术具有重要意义 研究，也是对制药行业，对人类健康。 有机硼化合物是有机合成中有用的构件。该硼基团为 能够适应各种立体特定的化学转化。更重要的是，空置的P- 硼原子的轨道可以稳定相邻碳原子中的阴离子或自由基。这 独特的性能促进了许多创新催化工艺的出现，以产生 富含对映体的有机硼酸盐。在这方面，我们小组建立了一个研究计划 以使用有机硼化合物的不对称合成为中心。我们特别致力于解决 手性分子对映选择性合成中的挑战 传统的方法。在这项提议中，我们寻求开发催化不对称转化 通过开发α-硼金属络合物的新反应性来使用有机硼化合物 α-硼基自由基。通过我们与计算化学专家的持续合作，我们 将进一步加深我们对反应机理的理解，这将引导我们朝着 变革性反应设计。与此同时，这些研究将允许获得富含对映体的 对有机合成有价值并与药物发现相关的分子。