Annulation Reactions of Alpha-Substituted Allylsilanes

α-取代的烯丙基硅烷的成环反应

• 批准号: 0315572
• 负责人: Keith Woerpel
• 金额: $ 39万
• 依托单位: University of California-Irvine
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 2003
• 资助国家: 美国
• 起止时间: 2003-06-01 至 2006-05-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=0315572&HistoricalAwards=false
• 关键词: Annulation; Reactions; Alpha; Substituted; Allylsilanes

The focus of this research involves the preparation of enantiomerically pure allylic silanes and the use of these compounds in annulation reactions for the production of five-and six-membered rings containing stereochemically defined tetrasubstituted carbons. The resulting compounds can serve as important intermediates for the synthesis of the natural products. This sequence will be used for the production of the natural product erythronolide A. Other studies will lead to the development of methodology for catalytic, enantioselective annulation reactions, for the preparation of cyclic peroxides, for the construction of 1,3-diamines, for annulations involving three-membered ring electrophiles and for the use of alpha-alkoxy allylic silanes in annulation reactions.With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Keith A. Woerpel of the Department of Chemistry at the University of California-Irvine. Dr. Woerpel will focus his work on developing methodology for establishing stereochemistry at tetrasubstituted carbon atoms in five- and six-membered rings as well as in acyclic systems. These reactions will be applicable to the synthesis of complex, biologically active natural products and will thus have broader impacts in the pharmaceutical industry. The project also provides an excellent venue for the training of undergraduate, graduate and postgraduate students.

本研究的重点涉及对映体纯烯丙基硅烷的制备以及这些化合物在环化反应中的用途，用于生产含有立体化学定义的四取代碳的五元和六元环。 所得化合物可作为天然产物合成的重要中间体。 该序列将用于生产天然产物赤酮内酯 A。其他研究将导致催化、对映选择性环化反应、环状过氧化物的制备、1,3-二胺的构建、涉及三元环亲电子试剂的环化以及在环化反应中使用 α-烷氧基烯丙基硅烷的方法的开发。 高分子化学项目正在支持加州大学欧文分校化学系 Keith A. Woerpel 博士的研究。 Woerpel 博士的工作重点是开发在五元环和六元环以及无环系统中的四取代碳原子上建立立体化学的方法。这些反应将适用于复杂的、具有生物活性的天然产物的合成，从而对制药行业产生更广泛的影响。 该项目还为本科生、研究生和研究生的培养提供了绝佳的场所。