Dr. Joseph Crockett
Degree Award Date
Reduction, Prochiral Ketones, alcohols
The alcohol-induced reduction of a prochiral ketone was examined according to the Meerwein-Ponndorf-Verley mechanism. In the presence of aluminum isopropoxide, isopropyl alcohol was used to reduce 2-butanone to 2-butanol. The product samples were characterized using chiral column gas chromatography. The (R) and (SJ enantiomers of the 2-butanol were effectively separated, and a tartrate adaptation was attempted in order to induce chirality in the intermediate aluminum structure and possibly trigger a situation of enantiomeric excess. However, neither the addition of D-tartaric acid nor aluminum tartrate resulted in the (R) and (SJ enantiomeric reduction products expected. Further investigation of a mechanism for this adaptation is needed
Higgins, Sara E., "Investigation of the Reduction of Prochiral Ketones" (2002). Honors Projects. 358.