Stereoselective Synthesis of Organoboronates Through Olefin Transformations and Their Application Towards Biologically Active Targets

Abstract

This dissertation describes three methods towards the stereoselective synthesis of organoboronates, and their application towards pharmacological targets of interest. The first chapter describes the use of alkyl migrating groups and alkyl electrophiles in the synthesis of secondary boronic esters through a highly selective nickel-catalyzed three component conjunctive cross-coupling reaction. Products from this conjunctive cross-coupling reaction are then converted to two alkaloids through boron amination and annulation processes. The second chapter describes the platinum-catalyzed diastereoselective diboration of carbocyclic, heterocyclic, and bicyclic alkenes. This reaction proceeded under air and both a homogeneous and heterogeneous catalyst was employed. Application of this reaction towards synthesis of the nucleoside analog Aristeromycin is also described. The final chapter details the development of an inexpensive and easily synthesized chiral diazaborinine that provides stereoinduction across a wide range of concerted and stepwise cycloaddition processes, affording heterocyclic-boron containing products in high yield and selectivity. Transformations of resulting organoboronates are also described.