RUI: Development of Sulfur Ylide Technology

本项目主要研究硫酰化物作为亲核烷基酰转移剂的应用。所提出的试剂比目前依赖于使用取代基（稳定的烷基化物）和金属促进剂（亲电的烷基转移剂）来发生反应的方案更具亲核性。化学选择性和非对映选择性反应途径可以根据使用的任何一个磺胺或亚砜鎓促进剂来调整。探索的目标是各种转化的催化、不对称诱导和底物普遍性研究，包括从酮和醛形成氧环烷、从亚胺形成叠氮嘧啶、从活化烯烃形成环丙烷、从氧环烷形成氧环烷和从叠氮嘧啶形成氮杂啶。在有机和大分子化学项目的支持下，南阿拉巴马大学化学系的David Forbes教授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高效和有选择性地构建这种环状化合物，从而获得本身具有重要意义的分子结构，或者可以作为合成更复杂分子的中间体，这些分子构成了现代生化和制药研究的基础。福布斯教授实验室的研究主要由本科生进行，通过阿拉巴马州运动科学项目选拔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.