Work

Peptide-Catalyzed Conversion of Racemic Oxazol-5(4 H )-ones into Enantiomerically Enriched α-Amino Acid Derivatives

Year: 2014

Type: article

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.

Source: The Journal of Organic Chemistry

DOI: 10.1021/jo402828f

Authors: Anthony J. Metrano, Scott J. Miller

Institution: Yale University

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: National Science Foundation, Innovative Research Group Project of the National Natural Science Foundation of China