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 合成有机化学新化学、立体化学和 用于合成碳-碳键的区域选择性方法。 我们实验室的初步结果表明， 钯催化的环烯烃的烯丙基交叉偶联， 芳基、乙烯基和炔基卤化物，以及烯基三氟甲磺酸酯，可以 在温和的反应条件下以高产率进行，不含 异构体 有机钯化合物的能力， 适应各种重要的有机功能 基团和它们加成到具有高区域和 立体选择性表明这是一种特别有用新方法 碳-碳键形成的方法， 以任何其他方式影响本方法。 详细 建议研究这一进程的范围和局限性。 这一过程的分子内变化将被检查。 利用该化学的肝素化和碳环化序列 看起来特别有希望。 这种新方法具有巨大的 潜在的合成这种多样的药用和 生理上感兴趣的物质如生物碱，大麻素， 洋地黄素和多环芳烃。