36th Annual Student Research Conference
A Continuation of Studying the Evans Magnesium Chloride Catalyzed Anti-Aldol Reaction Computationally
Audrey R. Kneip
Dr. Stuart Winikoff, Faculty Mentor
Evans Aldol reactions are commonly used in pharmaceutical practices as they allow the stereoselective generation of carbon-carbon bonds. We are specifically interested in Evans aldol reactions, which make use of oxazolidine ketones and can generate syn- and anti- products. Catalysts that produce syn-aldols are extensively studied and widely used; however, anti-aldol reactions are potentially just as useful, but not as widely studied. In order to create the desired reaction, magnesium chloride was introduced as a catalyst and was discovered to play a role as a Lewis acid within the reaction; causing the pKa to drop by approximately 36 units. The magnesium catalyst also reduces electron repulsion within the system, favoring the formation of pi-stacking complexes. After verifying the role of magnesium within the system, methyl groups were added in order to determine the influence of magnesium catalyst on stereochemistry, as the methyl introduces syn- and anti- stereochemistry to the system.
Keywords: Organic Chemistry, Computational Chemistry, Aldol Reaction
Topic(s):Chemistry
Presentation Type: Poster Presentation
Session: 4-1
Location: Student Union Building Activities Room
Time: 3:00