Development of selective non-metal based organocatalysts for asymmetric synthesis

This thesis is concerned with the design, synthesis and use of novel bifunctional organocatalysts for the asymmetric Michael addition of ketones and 1, 3 – dicarbonyl compounds to trans - β - nitrostyrene. Chapter 1 describes the concept of organocatalysis, including history and mode of action. A detailed review is provided on the organocatalytic Michael addition of carbon nucleophiles to nitroolefins. The bifunctional organocatalyst design and programme of work is also discussed. Chapter 2 details initial investigations conducted on the organocatalytic Michael addition of cyclohexanone to trans - β - nitrostyrene using monofunctional amine catalysts and hydrogen bond donor catalysts. Chapters 3, 4 and 5 depict the synthesis and testing of a range of novel bifunctional organocatalysts for the Michael addition of cyclohexanone to trans - β - nitrostyrene. Chapter 6 compares the different bifunctional organocatalysts and explores the scope of the catalysts and the Michael addition reaction.