Skip to main content
eScholarship
Open Access Publications from the University of California

UC Santa Barbara

UC Santa Barbara Previously Published Works bannerUC Santa Barbara

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.

Many UC-authored scholarly publications are freely available on this site because of the UC's open access policies. Let us know how this access is important for you.

Main Content
Current View