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C-H amidation of 2-aryl azlactones under iridium() catalysis: access to chiral amino acids

In this study, we examine the site-selctive iridium( iii )-catalyzed C-H amidation between 2-aryl azlactones and acyl azides. This transformation produces a range of ortho -amidated azlactones, which act as precursors for the synthesis of chiral amino acids via organocatalyzed ring-opening reactions...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2022-12, Vol.58 (96), p.13365-13368
Main Authors: Park, Min Seo, Chung, Eunjae, Mishra, Neeraj Kumar, Han, Sang Hoon, Han, Sangil, Kim, Saegun, Kim, In Su
Format: Article
Language:English
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Summary:In this study, we examine the site-selctive iridium( iii )-catalyzed C-H amidation between 2-aryl azlactones and acyl azides. This transformation produces a range of ortho -amidated azlactones, which act as precursors for the synthesis of chiral amino acids via organocatalyzed ring-opening reactions. To test its effectiveness, the method developed is applied to the late-stage C-H amidation of complex drug molecules. The isolation of an iridacycle species supports a proposed reaction pathway. First application of azlactone as a directing group in Ir( iii )-catalyzed C-H amidation is described herein. A noteworthy aspect of this method is the synthesis of chiral N -amidobenzoyl amino acids with high enantiomeric excess via organocatalysis.
ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc05245h