ORA Thesis: "Asymmetric conjugate addition reactions" - uuid:9e619a66-6277-48c2-8a2e-24f8206e52b3




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Reference: Scott A. Bentley, (2011). Asymmetric conjugate addition reactions. DPhil. University of Oxford.

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Title: Asymmetric conjugate addition reactions


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-(α-methylbenzyl)amino group as a chi- ral auxiliary, by employing the attempted conjugate additions of both N-benzyl-N-(α- methylbenzyl)hydrazine and N -benzyl-N -(α-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 -(α-methylbenzyl)amide. The isoxazolidin-5-ones are then globally de- protected via hydrogenolysis, giving rise to the corresponding β2,2,3-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 α,β-unsaturated ester. Finally, cyclisation of the β-N-arylamino esters to the corresponding tetrahydroquinolines is explored, and an application to the synthesis of the natural product (−)-angustureine is presented.

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

Digital Origin:Born digital
Type of Award:DPhil
Level of Award:Doctoral
Awarding Institution: University of Oxford
About The Authors
institutionUniversity of Oxford
facultyMathematical,Physical & Life Sciences Division - Chemistry - Organic Chemistry
researchGroupProf. S. G. Davies
oxfordCollegeNew College
Prof Stephen G. Davies More by this contributor
Bibliographic Details
Issue Date: 2011
Copyright Date: 2011
Urn: uuid:9e619a66-6277-48c2-8a2e-24f8206e52b3
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Member of collection : ora:thesis
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Copyright Holder: Scott Bentley
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