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. 2008 Sep 5;73(17):6506-12.
doi: 10.1021/jo801208m. Epub 2008 Jul 30.

Superacid-promoted reactions of alpha-ketoamides and related systems

Kiran Kumar Solingapuram Sai  1 , Pierre M Esteves, Eduardo Tanoue da Penha, Douglas A Klumpp
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Superacid-promoted reactions of alpha-ketoamides and related systems

Kiran Kumar Solingapuram Sai et al. J Org Chem. .

Abstract

The superacid-promoted reactions of alpha-hydroxy and alpha-ketoamides have been studied. Ionization of these compounds leads to varied aryl-substituted oxyindole products. In some cases, electrocyclization can lead to substituted fluorene products. Dicationic, superelectrophilic intermediates are proposed as intermediates leading to the products from alpha-hydroxy and alpha-ketoamides.

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