Sequential Reactions of Main Group Element Substituted Dienes

Wake Forest University, Winston Salem NC

Investigators

Abstract

This project will continue work on the development of catalytic, exo selective and enantioselective Diels-Alder reactions. Boron and silicon-substituted dienes, which offer practical advantages over transition metal-substituted dienes in terms of cost and disposal, will be prepared and utilized in catalytic chemistry and tandem reactions. These dienes can be used to reverse the normal endo selectivity of Diels-Alder reactions and provide access to new cycloadduct stereoisomers in high yield, diastereoselectivity and enantioselectivity. This synthetic method will provide access to relative and absolute cycloadduct stereochemistries that were not readily available previously through endo-selective Diels-Alder reactions of the polymerization-prone Z-dienes. With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Professor Mark Welker of the Department of Chemistry at Wake Forest University. Professor Welker's research efforts revolve around the development of tandem Diels-Alder/hydrolysis and Diels-Alder/cross coupling reactions. The products of these tandem reactions have biological activities ranging from insect anti-feedants to biomedical science applications. The successful development of the methodology therefore will have an impact on synthesis in the pharmaceutical and agricultural industries.