Carbohydrate-Catalyzed Enantioselective Alkene Diboration and Its Synthetic Application:

Thesis advisor: Marc L. SnapperThis dissertation will present four main projects that I have been working on since January 2015. The first two chapters will be focusing on the developments of the carbohydrate-catalyzed enantioselective alkene diboraiton. The exchange catalysis between carbohydrate-derived diol catalyst and diboron starting material renders the alkene diboration reaction possible without the aid from transition metals. This successfully brought down the cost for the enantioselective alkene diboration, making it an appealing tool for alkene transformation. Detailed mechanistic study that leads to the reaction efficiency improvements were discussed in chapter 2. The third chapter of this dissertation is about the developments of site-selective oxidation of 1,2-bis(boronate). This is a new type of a reaction motif that the alkene diboration product can undergo. The secondary boronic ester of the 1,2-bis(boronate) was selectively oxidized to hydroxyl group while leaving the primary boronic ester untouched. This new reaction opens up a variety of opportunities to transform 1,2-bis(boronate) into different functional groups. Lastly, in the fourth chapter, recent synthetic methods developed in the Morken group was used in the total synthesis study of complex natural product Amphidinolide C. As it is disclosed, the carbohydrate-catalyzed enantioselective alkene diboration proved to be a powerful transformation either in early stage starting material preparation or in late stage complex structure motif functionalization.Thesis (PhD) — Boston College, 2020.Submitted to: Boston College. Graduate School of Arts and Sciences.Discipline: Chemistry