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Issue 7, 2015
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Brønsted base-catalyzed α-oxygenation of carbonyl compounds utilizing the [1,2]-phospha-Brook rearrangement

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Abstract

A novel α-oxygenation reaction of carbonyl compounds was developed by utilizing the [1,2]-phospha-Brook rearrangement under Brønsted base catalysis. The reaction proceeds via the oxidation of enolates followed by the [1,2]-phospha-Brook rearrangement to afford α-oxygenated ester derivatives from easily accessible substrates having high functional group tolerance. In addition, the atom-economical tandem reaction of α-diethylphosphono ester derivatives with oxaziridines, which involves a carbon–carbon forming process in addition to α-oxygenation, was established under the low temperature conditions.

Graphical abstract: Brønsted base-catalyzed α-oxygenation of carbonyl compounds utilizing the [1,2]-phospha-Brook rearrangement

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Article information


Submitted
03 Apr 2015
Accepted
24 Apr 2015
First published
29 Apr 2015

Org. Chem. Front., 2015,2, 801-805
Article type
Research Article

Brønsted base-catalyzed α-oxygenation of carbonyl compounds utilizing the [1,2]-phospha-Brook rearrangement

A. Kondoh and M. Terada, Org. Chem. Front., 2015, 2, 801
DOI: 10.1039/C5QO00108K

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