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Title: Synthesis of Oxo-Amino Acids by Fukuyama Coupling
Author: Pickavance, Paul
ISNI:       0000 0001 3489 9155
Awarding Body: University of Sheffield
Current Institution: University of Sheffield
Date of Award: 2007
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This thesis describes the development of the Fukuyama coupling reaction of amino acid derived organozinc iodides i and amino acid derived aryl thiol esters ii to access a range of orthogonally protected oxo-bis-amino acids iii. Pentafluorophenylthiol esters (eg iv) have been developed as alternative electrophiles in this reaction and give improved yields when compared with their non-fluorinated analogues. Application of this coupling process was then undertaken in the synthesis of the alanine-alanine dipeptide isostere v, and a range of azabicyc1o[X.Y.O]alkane amino acids, of which vi was successfully prepared.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available