Aslam, O; (2012) Development of catalytic aza enolate reactions. Doctoral thesis , UCL (University College London).

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Abstract

This thesis describes the development of catalytic aza enolate reactions and a study of their applications in a range of reactions. Detailed herein are advances in three main areas of aza enolate chemistry, namely; the development of a novel catalytic aza enolate aldol reaction; the investigation of aza enolate reactions with challenging electrophiles (such as epoxides); and the discovery of a multi-component reaction for the formation of oxazolidines. The first chapter gives a brief overview of organocatalysis, summarising the main activation modes. This is followed by a detailed overview of aza enolate chemistry. The second chapter describes the development of a catalytic aza enolate aldol reaction. This methodology was explored in more detail with different substrates and asymmetry was investigated, with varying degrees of success. The third chapter describes the study of aza enolate reactions with a variety of challenging electrophiles. With epoxides and their derivatives, encouraging results were obtained. A new 3-component synthesis of oxazolidines from amines, ketones and epoxides was discovered during the course of this work and the synthesis of several novel oxozolidines was investigated.

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