Sequential Reactions of Main Group Element Substituted Dienes

该项目将继续开发催化、外选择性和对映体选择性的Diels-Alder反应。与过渡金属取代的二烯相比，硼和硅取代的二烯在成本和处理方面具有实用的优势，将被制备并用于催化化学和串联反应。这些二烯可以用来逆转Diels-Alder反应正常的Endo选择性，并提供高产率、非对映选择性和对映体选择性的新的环加成立体异构体。这种合成方法将提供相对和绝对的环加成立体化学，这是以前通过易于聚合的Z-双烯的内选择性Diels-Alder反应不容易获得的。通过这一奖项，有机化学和高分子化学项目支持维克森林大学化学系马克·韦尔克教授的研究。韦尔克教授的研究主要围绕串联Diels-Alder/水解反应和Diels-Alder/交叉偶联反应的发展展开。这些串联反应的产物具有从昆虫拒食到生物医学应用的各种生物活性。因此，该方法的成功开发将对制药和农业中的合成产生影响。

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.