A Studies towards the formation of asymmetric quaternary centres via radical allylation B Applications of chiral hydrazide organocatalysts to Diels-Alder, hydride reduction, and alpha-chlorination reactions C Studies directed towards the synthesis of potential HIV-1 reverse transcriptase inhibitors: 9-Alkylaryl TIBO derivatives

Abstract

In part A, the attempts at synthesizing quaternary centres via radical reactions are described. Using tartrate acetals as chiral auxiliaries, tertiary bromides were submitted to radical allylation conditions in an effort to form 1,3-dicarbonyl compounds 27 possessing an asymmetric quaternary centre at C2.* Part B describes the synthesis of chiral hydrazide 129 and its ability to catalyze the Diels-Alder reaction is examined. The application of chiral hydrazides 131 to the organocatalytic hydride reduction of alpha,beta-unsaturated aldehydes and the alpha-chlorination of aldehydes is also recounted herein.* Finally, in Part C, efforts towards the synthesis of potential broad spectrum HIV-1 reverse transcriptase inhibitors are described. Compounds 161 are based on the TIBO family of compounds and possess a novel alkylaryl appendage.* *Please refer to dissertation for diagrams.