Annulation Reactions of Alpha-Substituted Allylsilanes

这项研究的重点是制备对映体纯烯丙基硅烷，并将这些化合物用于环化反应，生成含有立体化学定义的四取代碳的五元环和六元环。所得化合物可作为合成天然产物的重要中间体。这一序列将用于生产天然产物赤藓内酯A。其他研究将导致开发用于催化、对映选择性环化反应、制备环状过氧化物、构建1，3-二胺、涉及三元环亲电体的环化反应以及在环化反应中使用α-烷氧基烯丙基硅烷的方法学。凭借这一奖项，有机和高分子化学计划将支持加州大学欧文分校化学系的Keith A.Woerpel博士的研究。维尔佩尔博士将致力于开发在五元环、六元环以及非环系中的四取代碳原子上建立立体化学的方法学。这些反应将适用于合成复杂的、具有生物活性的天然产物，因此将在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一个极好的场所。

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.