This project will continue the development of methods involving gem-dichloroepoxide intermediates for the safe and economical preparation of substituted carbonyl compounds and biomolecule analogs. Established routes to such materials generally require inefficient reaction steps, expensive reagents, or dangerous reaction conditions. Studies to establish safer and shorter methods for homologating carboxylic acids and preparing beta-amino acids, deoxy-C-glycosides and amino-C-glycosides from readily available trichloromethyl carbinols will be explored. The resultant products will be evaluated in terms of yield, preparation cost, and the stereo- and regioselectivities of devised reaction steps. Structure-reactivity analyses and product analyses under carefully adjusted reaction conditions will also demonstrate how specific parameters affect the formation and reactivity of the transient gem-dichloroepoxide intermediates involved in each method.
With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Professor Timothy Snowden of the Department of Chemistry at The University of Alabama. Professor Snowden's research efforts revolve around providing safer and more efficient methods to prepare synthetically versatile substituted carbonyl compounds, and therapeutically valuable unnatural amino acids and heterocycles. These methods will offer marked improvements in environmental influence, operational safety, and materials costs over currently employed approaches. Successful development of the methodology will have an impact on synthesis in academic research programs and in the pharmaceutical, agrochemical, and materials science fields.
