STEREOSPECIFIC SUZUKI-MIYAURA CROSS-COUPLING OF CHIRAL BENZYLIC BORONIC ESTERS AND VINYL BROMIDES

Abstract

The Suzuki-Miyaura cross-coupling reaction is a powerful method for the construction of carbon-carbon bonds in academia and industry. Despite extensive research in this area and the significance of the reaction, it is most often employed to prepare flat, Csp2-Csp2 bonds between two aryl groups. Since most bioactive compounds contain several 3-D or chiral centers, it is more desirable to make bonds between sp2-sp3 and sp3-sp3 carbon centers. However, when dealing with sp3 carbons in cross-coupling chemistry, new challenges arise such as β-hydride elimination, an undesirable side reaction. In 2009, our group reported the first example of a stereospecific coupling between chiral secondary boronic esters and aryl iodides. In this thesis, we report our investigations towards expanding the scope of our established Csp2-Csp3 coupling reaction with chiral boronic esters. By employing vinyl halides as electrophiles, we can stereospecifically prepare alkene-containing products—a useful handle for further functionalization.