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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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Published in: | Chemical communications (Cambridge, England) England), 2022-12, Vol.58 (96), p.13365-13368 |
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Main Authors: | , , , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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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. |
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ISSN: | 1359-7345 1364-548X |
DOI: | 10.1039/d2cc05245h |