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. 2008 Jul 17;10(14):3049-52.
doi: 10.1021/ol8010248. Epub 2008 Jun 14.

A nonenzymatic acid/peracid catalytic cycle for the Baeyer-Villiger oxidation

Gorka Peris  1 , Scott J Miller
Affiliations

A nonenzymatic acid/peracid catalytic cycle for the Baeyer-Villiger oxidation

Gorka Peris et al. Org Lett. .

Abstract

The combined action of carbodiimide and hydrogen peroxide upon exposure to carboxylic acid catalysts serves to generate transient peracids that can be engaged in the Baeyer-Villiger rearrangement of ketones to lactones. Up to 35 turnovers of the catalytic cycle may be achieved. The conditions are especially useful in the context of reactive cyclohexanones, and allow the use of H2O2 as the terminal oxidant. A singular example of a chiral catalyst demonstrates, in principle, that enantioselective catalysis will be possible with this strategy for catalyst turnover.

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Figures

Scheme 1
Scheme 1
Peracid BV Oxidation of Cyclic Ketones
Scheme 2
Scheme 2
A Catalytic Cycle for the BV Oxidation
Scheme 3
Scheme 3
Preliminary study of enantioselective BV.
See this image and copyright information in PMC

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