期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 79, 期 4, 页码 1542-1554出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo402828f
关键词
-
资金
- National Science Foundation Graduate Research Fellowship Program
- National Science Foundation [CHE-0848224]
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.
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