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Enantiopure Synthesis of Side Chain-Modified α-Amino Acids and 5-cis-Alkylprolines

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journal contribution
posted on 20.02.2016, 19:20 by Amar R. Mohite, Ramakrishna G. Bhat
A short, concise synthesis of enantiopure, side chain-modified α-amino acids such as 4-oxo-l-norvaline, 6-oxo-l-homonorleucine, and 5-cis-alkyl prolines is described. Knoevenagel condensation of l-aminocarboxylate-derived β-ketoesters with aldehydes followed by reductive decarboxylation results in unnatural α-amino acids in good yield. A fluorescent amino acid is synthesized using a similar protocol. These studies show that aminocarboxylate-derived β-ketoesters are very useful intermediates and the method employed is both general and practical for the preparation of γ­(δ)-oxo α-amino acids and alkylprolines.