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Issue 10, 2013
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Electrophilic α-oxygenation reaction of β-ketoesters using N-hydroxycarbamates: control of the ambident reactivity of nitrosoformate intermediates

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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.

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

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Supplementary files

Article information


Submitted
13 Jun 2013
Accepted
23 Jul 2013
First published
24 Jul 2013

Chem. Sci., 2013,4, 3857-3862
Article type
Edge Article

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

C. P. Frazier, D. Sandoval, L. I. Palmer and J. Read de Alaniz, Chem. Sci., 2013, 4, 3857
DOI: 10.1039/C3SC51658J

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