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.
Published Web Locationhttps://doi.org/10.1039/c3sc51658j
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.