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J Org Chem. 2014 Feb 21;79(4):1542-54. doi: 10.1021/jo402828f. Epub 2014 Feb 12.

Peptide-catalyzed conversion of racemic oxazol-5(4H)-ones into enantiomerically enriched α-amino acid derivatives.

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1
Department of Chemistry, Yale University , New Haven, Connecticut 06520-8107, United States.

Abstract

We report the development and optimization of a tetrapeptide that catalyzes the methanolytic dynamic kinetic resolution of oxazol-5(4H)-ones (azlactones) with high levels of enantioinduction. Oxazolones possessing benzylic-type substituents were found to perform better than others, providing methyl ester products in 88:12 to 98:2 er. The mechanism of this peptide-catalyzed process was investigated through truncation studies and competition experiments. High-field NOESY analysis was performed to elucidate the solution-phase structure of the peptide, and we present a plausible model for catalysis.

PMID:
24517453
DOI:
10.1021/jo402828f
[Indexed for MEDLINE]
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