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

被引：55
作者：
Metrano, Anthony J. [1 ]
Miller, Scott J. [1 ]
机构：
[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 04期
基金：
美国国家科学基金会;
关键词：
DYNAMIC KINETIC RESOLUTION; ASYMMETRIC ORGANIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; RACEMIC AZLACTONES; ORGANOCATALYSTS; RACEMIZATION; ALCOHOLYSIS; BROMINATION; HYDROLYSIS; ENZYMES;
D O I：
10.1021/jo402828f
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：1542 / 1554
页数：13
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