RUI: Stereochemical Determinants in Elimination and Proton Transfer Reactions

有机和大分子化学项目授予卡尔顿学院化学系的Jerry R. Mohrig教授这项本科院校研究奖，以表彰他对消除反应和质子转移反应中立体化学决定因素的研究。这些研究的重点是涉及丁酸的-取代酯和硫酯以及相关醛和酮的加成和消除反应的立体化学，旨在全面了解羰基和C-3取代基对涉及无环-取代羰基化合物的加成-消除和质子转移反应的立体化学影响。在一组本科化学专业学生的研究中，底物酸度和离去基在决定碱催化1,2-消除反应产生共轭羰基化合物的立体选择性中的重要性将通过合成和核磁共振光谱研究相结合来探索。同样，将研究亲电攻击在烯酸盐阴离子上的立体化学。了解和控制非环分子的三维结构仍然是有机化学的一个重要挑战。在此背景下，涉及分子中片段的添加或消除的反应的立体化学细节既具有基本的兴趣，又与许多生物催化过程相关。卡尔顿学院化学系的Jerry R. Mohrig教授因其对此类反应的立体化学研究而获得了有机和大分子化学项目颁发的本科生研究奖。通过化学专业本科生进行的合成和光谱研究的结合，Mohrig教授对这些重要的化学过程有了详细的了解，同时为本科生提供了对前沿重大问题进行研究的机会。

With this Research at Undergraduate Institutions award, the Organic and Macromolecular Chemistry Program is supporting Professor Jerry R. Mohrig, of the Department of Chemistry at Carleton College, for his studies of stereochemical determinants in elimination and proton transfer reactions. These studies, focused on the stereochemistry of addition and elimination reactions involving beta-substituted esters and thioesters of butyric acid and the related aldehydes and ketones, seek a comprehensive understanding of the stereochemical consequences of the carbonyl group and substituents at C-3 on the stereochemistry of addition-elimination and proton transfer reactions involving acyclic beta-substituted carbonyl compounds. In research to be carried out by a group of undergraduate chemistry majors, the importance of substrate acidity and the leaving group in determining the stereoselectivity of base-catalyzed 1,2-elimination reactions producing conjugated carbonyl compounds will be explored through a combination of synthetic and NMR spectroscopic studies. Similarly, the stereochemistry of electrophilic attack at enolate anions will be investigated.Understanding and controlling the three-dimensional structure of noncyclic molecules remains an inportant challenge in organic chemistry. Within this context, the stereochemical details of reactions involving the addition to or elimination of fragments from molecules are of both fundamental interest and relevance to numerous biologically catalyzed processes. Professor Jerry R. Mohrig, of the Department of Chemistry at Carleton College, is supported by a Research at Undergraduate Institutions award from the Organic and Macromolecular Chemistry Program for his studies related to the stereochemistry of such reactions. Through a combination of synthetic and spectroscopic studies, carried out by undergraduate chemistry majors, Professor Mohrig is developing a detailed understanding of these important chemical processes while simultaneously providing undergraduates with the opportunity to carry out research on fore-front, significant problems.