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Title: Enantioselective synthesis of non-biaryl atropisomers
Author: Fugard, Alison
ISNI:       0000 0004 7654 6931
Awarding Body: University of Oxford
Current Institution: University of Oxford
Date of Award: 2019
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This thesis describes the development of novel methods to synthesise non-biaryl atropisomers enantioselectively. In Chapter 1, atropisomerism is defined and explored, with a focus on non-biaryl atropisomers and the literature stereoselective syntheses of chiral naphthamides. Chapter 2 discusses initial attempts to synthesise chiral naphthamides using phase-transfer catalysis, and the barriers to rotation of intermediate enol ethers, and benzylated and debenzylated naphthols are determined. Chapter 3 concerns investigations into the low barriers to rotation of these debenzylated naphthols. Chapter 4 builds on this work to develop an enantioselective synthesis of benzylated naphthamides via a dynamic kinetic resolution of the naphthol starting material. This reaction was tested on a wide variety of substrates to determine its scope and limitations, and the barriers to rotation of the chiral products were calculated.
Supervisor: Smith, Martin D. Sponsor: Engineering and Physical Sciences Research Council
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Chemistry, Organic