This thesis is concerned with the asymmetric conjugate addition reactions of a range of chiral nucloeophiles.

Chapter 1 introduces the conjugate addition reaction as a valuable carbon-carbon and carbon-heteroatom bond forming reaction in organic chemistry, and explores the asymmet- ric conjugate addition of a range of chiral and achiral carbon and nitrogen nucleophiles to a range of acceptors.

Chapter 2 explores the use of the N-benzyl-N-(\u03B1-methylbenzyl)amino group as a chi- ral auxiliary, by employing the attempted conjugate additions of both N-benzyl-N-(\u03B1- methylbenzyl)hydrazine and N -benzyl-N -(\u03B1-methylbenzyl)hydroxylamine as chiral ammo- nia and water equivalents respectively.

Chapter 3 describes the asymmetric and stereoselective preparation of a range of 4,4- disubstituted isoxazolidin-5-ones from the conjugate addition of lithium (S)-N-tert-butyl- dimethylsilyloxy-N -(\u03B1-methylbenzyl)amide. The isoxazolidin-5-ones are then globally de- protected via hydrogenolysis, giving rise to the corresponding \u03B2^2,2,3-amino acids.

Chapter 4 focuses on the development of a protocol to effect the conjugate addition of a chiral aniline equivalent. The scope of the reaction is delineated by varying both the nu- cleophile and the \u03B1,\u03B2-unsaturated ester. Finally, cyclisation of the \u03B2-N-arylamino esters to the corresponding tetrahydroquinolines is explored, and an application to the synthesis of the natural product (\u2212)-angustureine is presented.

Chapter 5 contains full experimental procedures and characterisation data for all com- pounds synthesised in Chapters 2, 3 and 4.