RUI: Development of Sulfur Ylide Technology

本计画主要研究硫叶立德作为亲核烷叉转移剂的应用。所提出的试剂比目前的方案更亲核，目前的方案依赖于使用取代基（稳定的叶立德）和金属促进剂（亲电子的亚烷基转移剂）进行反应。化学选择性和非对映选择性反应途径可以根据锍或氧化锍促进剂的使用来调整。目标是探索各种转化的催化、不对称诱导和底物一般性研究，包括从酮和醛形成环氧乙烷、从亚胺形成氮丙啶、从活化烯烃形成环丙烷、从环氧乙烷形成氧杂环丁烷和从氮丙啶形成氮杂环丁烷。在有机和大分子化学计划的RUI奖的支持下，大卫福布斯教授，南亚拉巴马大学化学系的，正在开发合成含有三元环的分子的新方法。使用含硫试剂，福布斯教授和他的学生能够有效地和选择性地构建这样的环状化合物，从而获得分子结构，这些结构本身是重要的，或者可以作为合成更复杂分子的中间体，形成现代生物化学和药物研究的基础。福布斯教授实验室的研究主要由本科生进行，通过亚拉巴马科学运动项目选出的一名地区高中教师也将参与其中。

This project focuses on the use of sulfur ylides as nucleophilic alkylidene transfer agents. The reagents proposed are more nucleophilic than current protocols which rely of on the use of substituents (stabilized ylides) and metal promoters (electrophilic alkylidine transfer agents) for reaction to occur. Chemoselective and diastereoselective reaction pathways can be tuned depending upon use of either sulfonium or sulfoxonium promoter. Targeted for exploration are catalysis, asymmetric induction, and substrate generality studies for a variety of transformations, including the formation of oxiranes from ketones and aldehydes, aziridines from imines, cyclopropanes from activated alkenes, oxetanes from oxiranes and azetidines from aziridines.With the support of this RUI award from the Organic and Macromolecular Chemistry Program, Professor David Forbes, of the Department of Chemistry at the University of South Alabama, is developing new methods for the synthesis of molecules containing three-membered rings. Using sulfur-containing reagents, Professor Forbes and his students are able to construct such cyclic compounds efficiently and selectively, affording access to molecular structures which are themselves significant or which can serve as intermediates in the synthesis of the more complex molecules forming the basis of modern biochemical and pharmaceutical research. Research in Professor Forbes' laboratory is carried out primarily by undergraduates, and an area high school teacher, selected through the Alabama Science in Motion program, will also be involved.