Synthesis and use of heterocycles in organocatalysis

• Main Author: Davies, Huw John
• Published: Cardiff University 2009
• Subjects: 541.39
• Online Access: http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.584595

This thesis is concerned with two sections: the first deals with the synthesis of quinolinones via a tandem VNS reaction. The second examines the aminocatalysis of the Baylis-Hillman reaction Chapter 1: Provides an overview of aromatic chemistry. Focus is on the separate mechanisms of the substitution of aromatic compounds. An overview of VNS chemistry is also included to provide a basis for the investigations carried out. Chapter 2: Describes the synthesis of a small library of 6/s-rutroaromaric compounds using the VNS reaction. An investigation into the cyclisation of the &w-nitroaromatic compounds to a range of biologically interesting quinolinones is also described. Chapter 3: Introduces the concept of aminocatalysis and gives an overview of recent developments in the field including the Baylis-Hillman reaction, the reaction chosen for asymmetric catalyst development. Chapter 4: Is split into three sections the first describes an interesting solvent effect encountered during the course of the investigation. The second investigates the effect of the structure of secondary amines on the enantioselectivity of the reaction via iminium ion formation. The third section describes the investigation of the structure of Lewis bases on the enantioselectivity of the reaction.