Dehydration and amination of alpha-, beta-dihydroxy carbonyl compounds to alpha-amino acids

Abstract

Processes are disclosed for the synthesis of an α-amino acid or α-amino acid derivative, from a starting compound or substrate having a carbonyl functional group (C═O), with hydroxy-substituted carbon atoms at alpha (α) and beta (β) positions, relative to the carbonyl functional group. According a particular embodiment, an α-, β-dihydroxy carboxylic acid or carboxylate is dehydrated to form a dicarbonyl intermediate by transformation of the α-hydroxy group to a second carbonyl group (adjacent a carbonyl group of the starting compound) and removal of the β-hydroxy group. The dicarbonyl intermediate is optionally cracked to form a second, in this case cracked, dicarbonyl intermediate having fewer carbon atoms relative to the dicarbonyl intermediate but preserving the first and second carbonyl groups. Either or both of the dicarbonyl intermediate and the cracked dicarbonyl intermediate may be aminated to convert the second carbonyl group to an amino (—NH) group, for producing the corresponding α-amino acid(s).