Syntheses of optically active 2-amino-4-oxobutyric acid and N,O-protected derivatives.
Strategies for the synthesis of optically active aspartaldehyde derivatives are reviewed. Most of them are using the chiral pool: allylglycine or naturally occurring homoserine, aspartic acid or methionine and side chain modifications. This will be developed in the first part. Some other original routes are also displayed in the second part. Different aspects of each strategy are discussed: the nature and number of steps, the problem of protecting groups, the price and availability of starting materials. Some synthetic applications of such interesting chiral synthons are shown in the last part.
Ecole Nationale Supérieure de Chimie de Paris, France. patmeffr@ext.jussieu.fr
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D000596:Amino Acids / Q000737:chemistry*; D001224:Aspartic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D000596:Amino Acids; D001224:Aspartic Acid; C006644:aspartic semialdehyde