Organocatalysis and green chemistry are major areas of modern research. The current project aims to apply these concepts to development of a catalytic Corey-Chaykovsky reaction. Chapter 1 provides an extensive review of current literature and an outline of the goals of the current research. In Chapter 2, a method has been developed for the Corey-Chaykovsky aziridination reaction using imine and sulfonium salt starting materials for the selective synthesis of vinylaziridine or aryl pyrroline. It has been shown that the choice of base used in the reaction plays a crucial role for product selectivity. Further investigations suggest that a rearrangement of vinylaziridine to pyrroline is unlikely, and the base used may activiate the intermediate molecule. In Chapter 3, a synthetic pathway has been developed for three target dihydrobenzothiophene sulfides to be used in the Corey-Chaykovsky reaction (one chiral sulfide). The core structure was synthesised but the sulfonium salt derivative could not be formed. Substituted derivatives not synthesised due to crucial steps being unsuccessful. However, the five new compounds were prepared and fully characterised, and alternative synthetic pathways have been proposed. In Chapter 4, three derivatives of pyrroline were synthesised with a future goal of using them as organocatalysts. A detosylation study was performed and needs further optimisation. The methods developed are adaptable for asymmetric synthesis to obtain enantiomerically pure samples of pyrrolidine suitable for use as an organocatalysts. In Chapter 5, the shortcomings of the working chapters (2-4) have been addressed and alternative synthetic strategies suggested, with particular emphasis on obtaining enantiomerically pure compounds, all with appropriate reference to evidence and precedent from the literature.