New Methods for Nitrogen and Oxygen Heterocycle Synthesis

氮氧杂环合成新方法

• 批准号: 8912659
• 负责人: Sherry R Chemler
• 金额: $ 32.46万
• 依托单位: STATE UNIVERSITY OF NEW YORK AT BUFFALO
• 依托单位国家: 美国
• 财政年份: 2006
• 资助国家: 美国
• 起止时间: 2006-07-01 至 2019-06-30
• 项目状态: 已结题
• 来源: https://reporter.nih.gov/project-details/8912659
• 关键词: Aerobic; Aldehydes; Alkenes; Amines; Area; Biomedical Research; Carbon; Central Nervous System Diseases; Collection; Complex; Copper; Coupling; Cyclization; Development; Development Plans; Drug Compounding; Drug Industry; Imines; In Situ; Ketones; Lactams; Lactones; Ligands; Metals; Methodology; Methods; Nitrogen; Organic Synthesis; Oxygen; Phenols; Potassium; Reaction; Ring Compound; Text; Time; Work; abstracting; base; catalyst; design; drug discovery; novel; oxidation; receptor; small molecule

Enter the text here that is the new abstract information for your application. This section must be no longer than 30 lines of text. New reactions for the synthesis of saturated oxygen and nitrogen heterocycles based on copper-catalyzed additions to readily available alkenes are being developed. The use of chiral copper complexes for stereocontrolled Csp3-O and Csp3-N bond formation is being explored. Based on our mechanistic work in this area, we have found that both polar and radical reaction mechanisms are involved, and judicious selection of substrate and reaction conditions can enable the concise and enantioselective synthesis of otherwise challenging complex molecules from simple alkenol and alkenylamine substrates. In this project, an enantioselective alkene carboetherification scope is expanded to useful oxygen heterocycles such as phthalans, compounds that have shown activity as 1 receptor ligands (relevant to CNS disorder therapy). The first highly enantioselective hydroalkoxylation of unactivated alkenes for the synthesis of chiral oxygen heterocycles is being developed. A diverse collection of novel chiral spirocyclic compounds is accessible from 1,1-disubstituted alkenes using a suite of copper-catalyzed intramolecular alkene difunctionalization reactions. In this context new copper-catalyzed enantioselective alkene dioxygenation and oxyamination reactions will be explored. Potentially powerful aerobic alkene oxidative difunctionalizations are also being explored. Copper-catalyzed intermolecular couplings between vinylarenes and alkyl radicals, formed in situ, are being explored for the synthesis of oxygen and nitrogen heterocycles. Lastly, an elusive catalytic enantioselective Mannich reaction with phenols is being pursued. The concise, enantioselective synthesis of bioactive saturated oxygen and nitrogen heterocyclic small molecules will be performed as a demonstration of the biomedical relevance of these reactions.

在此处输入文本，这是您的应用程序的新摘要信息。本节必须是否 超过30行的文本。 合成饱和氧和氮杂环化合物的新反应 基于铜催化的对容易获得的烯烃的加成正在被 开发手性铜络合物用于立体控制的Csp 3-O和 正在探索Csp 3-N键的形成。根据我们在这方面的机械工作， 区域，我们已经发现，极性和自由基反应机制是 所涉及的，并且明智地选择底物和反应条件可以使得 具有挑战性配合物的简洁和对映选择性合成 分子从简单的烯醇和烯基胺底物。在这个项目中，一个 将对映选择性烯烃碳醚化反应的范围扩大到有用氧 杂环化合物，如酞，已显示出活性的化合物， 受体配体（与CNS疾病治疗相关）。第一高 未活化烯烃的对映选择性加氢烷氧基化， 正在开发手性氧杂环。各种各样的小说集 手性螺环化合物可从1，1-二取代的烯烃使用 铜催化分子内烯烃双官能化反应。在 本发明涉及一种新的铜催化的对映选择性烯烃双氧化反应， 将探索氧胺化反应。潜在强力好氧烯烃 氧化双官能化也在探索中。铜催化 乙烯基芳烃和烷基之间的分子间偶联，原位形成， 正在探索用于氧和氮杂环的合成。最后， 一种难以捉摸的催化对映选择性曼尼希反应正在被研究 追求。具有生物活性的饱和氧的简明、对映选择性合成 和氮杂环小分子将作为示范进行 这些反应的生物医学相关性。