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Paper | Regular issue | Vol 65, No. 1, 2005, pp.59-75
Published online, 2nd November, 2004
DOI: 10.3987/COM-04-10214
3-Benzoyl-2-isopropyl-4-alkyloxazolidin-5-ones as Efficient and Inexpensive Sources of Enantiopure α,α-Dialkyl α-Amino Acids and α,β-Dialkyl α,β-Diaminopropionic Acids

Susana Rojas-Lima,* Omar Téllez-Zenteno, Heraclio López-Ruiz, Lizeth Loubet-González, and Alejandro Alvarez-Hernandez

*Chemical Research Center (CIQ), Autonomous University of Hidalog (UAEH), University City, Pachuca-Tulancingo Road Km 4.5, Pachuca de Soto, Hidalogo, CP 42076, Mexico

Abstract

It is shown that the 3-benzoyl-2-isopropyl-4-alkyloxazolidin-5-ones (12), derived from isobutyraldehyde and α-amino acids are as efficient as, but more economical than, the corresponding tert-butyl compounds (9), as sources of enantiopure α,α-dialkylated α-amino acids (e.g., 21-23). In the absence of alkylating agents, the anions of (2R,4S)-12 and its enantiomer undergo a fragmentation-recombination process to generate (1S,2’R,4’S)-N-[1-(3-benzoyl- 2-isopropyl-4-methyl-5-oxo-oxazolidin-4-yl)-2-methylpropyl]benzamide ((1S, 2’R,4’S)-20), and its enantiomer. Acidic methanolysis of these condensation products provides access to α,β-dialkylated α,β-diaminopropionic acids [e.g., (2S,3S)-2,3-bisbenzoylamino-2,4-dimethylpentanoic acid methyl ester ((2S,3S)-24)).