PALLADIUM-CATALYZED ALKYLATION OF CYCLOALKENES

钯催化的环烯烷基化

• 批准号: 3297335
• 负责人: RICHARD C. LAROCK
• 金额: $ 7.57万
• 依托单位: IOWA STATE UNIVERSITY
• 依托单位国家: 美国
• 财政年份: 1988
• 资助国家: 美国
• 起止时间: 1988-04-01 至 1993-03-31
• 项目状态: 已结题
• 来源: https://reporter.nih.gov/project-details/3297335
• 关键词: alkaloids; alkenes; alkylation; cannabinoids; carbopolycyclic compound; catalyst; cyclic compound; drug design /synthesis /production; isomer; organometallic compounds; palladium; prostaglandins; stereochemistry

Progress in medicine today relies heavily on the development in synthetic organic chemistry of new chemo-, stereo- and regioselective methods for the synthesis of carbon-carbon bonds. Preliminary results in our laboratories indicate that the palladium-catalyzed allylic cross-coupling of cyclic alkenes and aryl, vinylic and alkynyl halides, as well as alkenyl triflates, can be effected in high yield, under mild reaction conditions, free of isomers. The ability of organopalladium compounds to accommodate a wide variety of important organic functional groups and their tendency to add to alkenes with high regio- and stereoselectivity suggest this to be an exceptionally useful new approach to carbon-carbon bond formation which cannot be effected in any other way by present methodology. A detailed study of the scope and limitations of this process is proposed. Intramolecular variations of this process will be examined. Hetero- and carboannulation sequences utilizing this chemistry look particularly promising. This new methodology possesses vast potential for the synthesis of such diverse medicinally and physiologically interesting substances as alkaloids, cannabinoids, prostaglandins and polycyclic aromatic hydrocarbons.

当今医学的进步在很大程度上依赖于 新化学，立体和 碳碳键合成的区域选择性方法。 我们的实验室的初步结果表明 钯催化的环烷烃和 芳基，Vinylic和Alkynyl卤化物以及烷烯基三氧化酸盐可以 在轻度反应条件下以高收率作用，没有 异构体。 有机丙基化合物的能力 容纳各种重要的有机功能 小组及其倾向于将烷基添加到具有较高区域和高的烯烃的趋势 立体选择性表明这是一个非常有用的新的 碳碳键形成的方法 通过当前方法以任何其他方式实现。 详细的 提出了该过程的范围和局限性的研究。 将检查该过程的分子内变异。 利用这种化学的杂音和碳水化合物序列 看起来特别有希望。 这种新方法具有广阔的 潜在地综合了这种多样的药物和 生理上有趣的物质，例如生物碱，大麻素， 前列腺素和多环芳烃。