1. Stereoselective Tin-Free Radical Reactions
Jake Zimmerman, Department of Chemistry and Biochemistry, Ohio Northern University
In the last two decades the use of radical chemistry in organic synthesis has greatly increased. More recently, the study of enantioselective radical reactions has received much attention. Although there have been significant advances in the field of asymmetric radical processes, there are still many shortcomings. For instance, most of the literature reports require high catalytic loading, toxic reagents (organotin) and are limited in substrate scope. Due to these shortcomings, our group is interested in developing tin-free asymmetric radical processes.
One of our projects focuses on switching the usual reactivity pattern of enantioselective radical reactions in order to make the methodology more diverse and attractive to target molecule synthesis. We are currently investigating an asymmetric tin-free radical fragmentation reaction for the preparation of 1,4-dicarbonyl compounds.
Based on our interest in replacing tin reagents in radical reactions, we have shown that simple silanes can act as hydrogen atom sources in low temperature reductive asymmetric radical additions. These products contain one to three new stereocenters from a single transformation.