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

AJ Metrano, SJ Miller

Index: Metrano, Anthony J.; Miller, Scott J. Journal of Organic Chemistry, 2014 , vol. 79, # 4 p. 1542 - 1554

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Citation Number: 22

Abstract

We report the development and optimization of a tetrapeptide that catalyzes the methanolytic dynamic kinetic resolution of oxazol-5 (4 H)-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 ...