In the scope of our BACE1 inhibitor project we used an originally designed microtiter plate-based screening to discover 4 triazole-linked reduced amide isosteres that showed modest (single digit micromolar) BACE1 inhibition. Our ligands were designed based on a very potent (single digit nanomolar) isopththalamide ligand from Merck. We supplanted one of the amide linkages in order to incorporate our triazole and saw a 1000-fold decrease in potency. We then enlisted Molsoft, L.L.C. to compare our ligand to Merck's in silico to account for this discrepancy. They found that the triazole linkage gives rise to a significantly different docking pose in the active site of the BACE1 enzyme, therefore diminishing its potency relative to the Merck ligand. The ability to control the regio- and stereochemical outcome of organic reactions is an ongoing interest and challenge to synthetic chemists. The pre-association of reacting partners through hydrogen bonding (H-bonding) can often to yield products with extremely high stereoselectivity. We were able to show that anilines, due to their enhanced acidity relative to amines, can serve as substrate directing moieties in the opening of cyclohexene oxides. We observed that by judicious choice of conditions we could control the regiochemical outcome of the reaction. These studies demonstrate that an intramolecular anilino-NH hydrogen bond donor can direct Fürst-Plattner epoxide opening. A unified mechanism for this phenomenon has been proposed in this work which consists of a novel mechanistic route we call "NH-directed Fürst-Plattner." We further studied the opening of cyclohexene oxides by incorporating amide and amide derivative substituents in both the allylic and homoallylic position relative to the epoxide moiety. Our attempts to control regioselectivity in the allylic systems were unsuccessful; however when the directing substituent was in the homoallylic position, we could demonstrate some degree of regioselectivity. An additional project that the author worked on for approximately one year during his graduate student tenure is not described within this work. In February of 2009 AstraZeneca, Mayo Clinic, and Virginia Tech Intellectual Properties Inc. concomitantly announced that AstraZeneca licensed a portfolio of preclinical Triple Reuptake Inhibitor (TRI) compounds for depression. The lead compound, PRC200, was discovered by a collaborative effort between the Carlier and Richelson (Mayo Clinic Jacksonville) research groups in 1998. The author was tasked to develop backup candidates of PRC200 in order to improve the pharmacokinetics of the lead compound. Due to confidentiality agreements, this work is not reported herein. / Ph. D.