RUI: Development of Sulfur Ylide Technology

University Of South Alabama, Mobile AL

Investigators

Abstract

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.