This research involves the use of tellurium reagents for the production of enatiomerically pure organic compounds. By combining tellurium methodology with Sharpless kinetic resolutions or asymmetric epoxidations of allylic alcohols the following will be able to be achieved: (1) the synthesis of optically active secondary and tertiary allylic alcohols from achiral starting materials without resolution, (2) the synthesis of secondary cis allylic alcohols from trans compounds in high optical purity, (3) the conversion of racemic, secondary allylic alcohols to either enantiomer in high yield and high optical purity without the loss of material sustained in a kinetic resolution, (4) the deoxygenation of acetates of glycidols with retention of the chirality at the carbinol center, and (5) the transposition of double bond and alcohol functionalities in both the free alcohol as well as in the sulfonate esters of the allylic alcohols. Also, 2-substitued allylic alcohols whose accessibility by other methods is difficult will be prepared and studied. %%% With this award the Synthetic Organic Program of the Chemistry Division will support the research of Dr. Donald C. Dittmer of the Department of Chemistry at Syracuse University. The research is in the area of synthetic methodology and will utilize tellurium reagents for the production of organic substrates in optically pure form. Using a variety of approaches the work will allow the preparation of these optically pure compounds from optically inactive starting materials. This process is extremely important in modern synthetic chemistry because many of the target molecules which have biological activity must be prepared optically active to study their properties.
