2-芳基-2-硝基乙酸酯作为芳基硝甲烷、α-酮酯和α-氨基酸的中心前体。
2-Aryl-2-nitroacetates as central precursors to aryl nitromethanes, α-ketoesters, and α-amino acids.
机构信息
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.
出版信息
J Org Chem. 2013 Jan 18;78(2):717-22. doi: 10.1021/jo302071s. Epub 2013 Jan 2.
Abstract
Nitroarylacetates are useful small molecular building blocks that act as precursors to α-ketoesters and aryl nitromethanes as well as α-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 α-ketoesters, new mild conditions for the Nef disproportionation were identified.
摘要
硝酰基乙酸酯是一种非常有用的小分子构建模块，可作为α-酮酯和芳基硝基甲烷以及α-氨基酸的前体。开发了能够以良好收率生成这些化合物类型的方法。讨论了两种不同的脱羧条件，分别适用于具有中性和缺电子芳基基团的底物与富电子芳基基团的底物。对于α-酮酯的形成，确定了用于内夫歧化反应的新的温和条件。
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