Thesis advisor: James Morken / This dissertation details two different alkene difunctionalization strategies that are utilized in the synthesis of three types of organoboron species in racemic and enantioenriched fashion. Chapter one will introduce the carbohydrate and DBU co-catalyzed transition-metal-free enantioselective diboration reactions of unactivated alkenes. Mechanistic insights guided reaction condition design will be discussed. In chapter two, a nickel-catalyzed conjunctive cross-coupling of 9-BBN borane and carboxylic acid derivatives is presented. Its development and detailed mechanistic studies, along with the efforts in asymmetric induction will be covered. Finally, the first enantio- and diastereoselective synthesis of 1,2-anti-silylboronates enabled by palladium-catalyzed conjunctive cross-coupling will be described. The optimization of chemo-, enantio- and diastereoselectivity in the reactions and their following transformations (e.g. oxidation and amination) is demonstrated. / Thesis (PhD) — Boston College, 2020. / Submitted to: Boston College. Graduate School of Arts and Sciences. / Discipline: Chemistry.