Gray, P.J.; (2008) Novel tandem reactions of allenic substrates. Doctoral thesis , University of London.

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Abstract

This thesis describes the development of novel tandem reactions of allenic substrates, designed for the synthesis of structurally complex heterocyclic and carbocyclic systems together with the development of methodology for stereocontrolled preparation of functionalised olefins. Consequently, the thesis is divided into three sections. The first of these introduces the allenic functionality highlighting the special properties associated with allenic compounds and the recent advances in allene chemistry with particular emphasis on the application of allenic substrates to heterocyclisation, carbocyclisation and carbometallation. The second section describes the results obtained during the course of this study and is divided into three sub-sections. The first of these summarises the development of novel aza-annulation methodology for the preparation of biologically relevant nitrogen containing molecular architectures using electron deficient allenes as substrates for regioselective vinylogous urethane and amide formation. The application of this methodology towards the synthesis of the cytotoxic alkaloid N-oxo-rhazinilam is also discussed. This is followed by a discussion of a tandem enamine formation cyclisation sequence using allenic substrates for the preparation of substituted cyclopentanones. The final section describes a preliminary study of a novel carbometallation reaction of allenic substrates for stereocontrolled preparation of fiinctionalised alkenes. Chapter three provides a summary of these three areas of research as well as highlighting potential avenues for further exploration. Chapter four details all of the relevant experimental procedures and compound characterisations.

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