Development of selective non-metal based organocatalysts for asymmetric synthesis

• Main Author: Carley, Allison Patricia
• Published: University of Southampton 2007
• Subjects: 541.39
• Online Access: http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.484966

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 - ~ - 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 nucleophik~s to nitroolefins. The bifunctional organocatalyst design and programme ofwork is also discussed. Chapter 2 details initial investigations conducted on the organocatalytic Michael addition of cyclohexanone to trans - ~ - 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 rYfichael addition ofcyclohexanone to trans - ~ - nitrostyrene. Ch,:iptl~r 6 the different bifunctional organocatalysts and explores the scope rvIichael addition reaction.