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Electrophilic α-oxygenation reaction of β-ketoesters using N-hydroxycarbamates: Control of the ambident reactivity of nitrosoformate intermediates

  • Author(s): Frazier, CP;
  • Sandoval, D;
  • Palmer, LI;
  • De Alaniz, JR
  • et al.
Abstract

A copper-catalyzed aminooxylation of β-ketoesters using transient nitrosoformate intermediates is reported. The transformation is highly practical, efficient and highlights the ambident reactivity of nitrosocarbonyl compounds through a rare example of a nitrosocarbonyl aldol reaction. Along with a broad substrate scope, the reaction conditions that help control the regiochemistry are explored and the use of N-carbamate protected hydroxylamine is showcased by subsequent one-pot annulation reactions. © 2013 The Royal Society of Chemistry.

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