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Title: A versatile chemo-enzymatic route to enantiomerically pure β-branched-α-amino acids
Author: Roff, Geoffrey John
Awarding Body: University of Edinburgh
Current Institution: University of Edinburgh
Date of Award: 2004
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Enantiomerically pure β-branched-α-amino acids are important synthetic targets and a challenging group of compounds to prepare. A series of diastereoisomers of β-methylphenylalanine analogues have been prepared in enantiomerically pure form using a combination of chemo-and bio-catalysis. Starting from L-threonine methyl ester and proceeding via the vinyl halide with Suzuki chemistry, a range of β,β-disubstituted didehydroamino acids were obtained as their (Z)-isomers. Asymmetric hydrogenation of these alkenes, using either the [Rh(R,R)-Et-DuPhos(COD)BF4 or [Rh(S,S)-Et-DuPhos(COD)]BF4 catalyst, followed by hydrolysis, yielded two of the four possible sets of diastereoisomers of the β-branched amino acid. Subsequent stereoinversion, using a stereoselective amino acid oxidase in combination with a non-selective reducing agent, furnished the remaining two sets of diastereomers.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available