The Control of Acyclic Stereochemistry Employing Organophosphorus Auxiliaries

使用有机磷助剂控制无环立体化学

• 批准号: 9113711
• 负责人: Slayton Evans
• 金额: $ 53.94万
• 依托单位: University of North Carolina at Chapel Hill
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 1991
• 资助国家: 美国
• 起止时间: 1991-11-01 至 1997-04-30
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=9113711&HistoricalAwards=false
• 关键词: Control; Acyclic; Stereochemistry; Employing; Organophosphorus

The focus of this research is the development of carbon-carbon bond making processes that use organophosphorus moieties to control stereochemistry. Design of the auxiliaries strives to maximize chirality transfer while allowing recycling of the chiral auxiliaries. Activation of cyclic dioxaphosphoranes by site-selective complexation with silyl cations will afford substituted 1,2-diols with high regio- and stereospecificity. Control of acyclic stereochemistry using a phosphoryl group in concert with the Mukaiyama-Michael reaction is planned and the unique metallation/alkylation chemistry of spirooxyphosphoranes will be probed for both theoretical as well as synthetic gain. %%% With this renewal award, the Synthetic Organic Program is supporting the research of Dr. Slayton A. Evans of the Department of Chemistry at the University of North Carolina, Chapel hill. Professor Evans will focus his work on projects that center on the design of new and versatile stereoselective carbon-carbon bond making strategies all of which use organophosphorus moieties to control the stereochemical course of the reactions.

本研究的重点是利用有机磷基团控制立体化学的碳-碳键制造工艺的发展。助剂的设计力求使手性转移最大化，同时允许手性助剂的回收。通过与硅基阳离子的位置选择性络合活化环二磷烷将提供具有高区域和立体特异性的取代1,2-二醇。在Mukaiyama-Michael反应中使用一个磷酸基来控制无环立体化学，并对螺氧磷烷的独特金属化/烷基化化学进行理论和合成增益的探索。有了这个更新奖，合成有机项目正在支持北卡罗来纳大学教堂山分校化学系的斯雷顿·a·埃文斯博士的研究。Evans教授将把他的工作重点放在设计新的多功能立体选择碳-碳键制造策略上，所有这些策略都使用有机磷部分来控制反应的立体化学过程。