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Title: Asymmetric synthesis of α-amino acid derivatives
Author: Goubet, D. C. M.
Awarding Body: University College of Swansea
Current Institution: Swansea University
Date of Award: 1994
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A general background to α-amino acids is discussed in the first chapter. After a brief account on classification, properties and applications of these compounds, asymmetric processes leading to optically enriched residues are reviewed in detail. The second chapter describes the envisaged stereoselective approach towards these substrates involving Michael-type addition onto a chiral didehydroalanine derivative. Syntheses of α,β-unsaturated amino acids are reviewed after a brief section on Michael-type reactions. The preparation of a chiral didehydroamino acid residue has been investigated using camphor-based chiral auxiliaries and especially Oppolzer's sultam. This work is described in Chapter Three. Following these attempts, attention has been concentrated on N-(2-bromoalkanoyl)bornane-10,2-sultams. The diastereoselective one-step synthesis of these compounds has been optimized from racemic α-bromo acid derivatives and a new method of linking onto Oppolzer's auxiliary has been consequently developed as described in Chapter Four. The first two sections of Chapter Five deal with the properties of N-(2-bromoalkanoyl)bornane-10,2-sultams. Applications of these properties to the diastereoselective synthesis of α-heteroatom acid derivatives starting from optically pure or racemic α-bromo amides are discussed in the third part of Chapter Five.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available