4.7 Article

2-Aryl-2-nitroacetates as Central Precursors to Aryl Nitromethanes, α-Ketoesters, and α-Amino Acids

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 2, Pages 717-722

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo302071s

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Funding

  1. NIH [RO1GM087605]

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Nitroarylacetates are useful small molecular building blocks that act as precursors to alpha-ketoesters and aryl nitromethanes as well as alpha-amino acids. Methods were developed that produce each of these compound types in good yields. Two different conditions for decarboxylation are discussed for substrates with neutral and electron-poor aryl groups versus electron-rich aryl groups. For formation of the alpha-ketoesters, new mild conditions for the Nef disproportionation were identified.

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