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

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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… Click to show full abstract

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.

Keywords: amino acids; iridium iii; chiral amino; aryl azlactones; amidation aryl; amidation

Journal Title: Chemical communications
Year Published: 2022

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