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Baeyer Villiger Oxidation

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The Bayer-Villiger oxidation is a useful method for conversion of aldehydes and ketones to esters by the insertion of an oxygen atom from a peroxycarboxylic acid (RCO3H). For example, treating acetophenone with a peroxycarboxylic acid converts it to the ester phenyl acetate.

Baeyer Villiger Oxidation

Mechanism

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The Baeyer-Villiger oxidation is also widely used for synthesizing lactones from cyclic ketones. A common reagent used to carry out the Baeyer-Villiger oxidation is m-chloroperoxybenzoic acid. Certain other peroxycarboxylic acids can be used as well and we will discuss shortly a "green" variation of the Baeyer-Villiger oxidation by a peroxycarboxylic acid.

The following is a mechanism proposed for Baeyer-Villiger oxidation by a peroxycarboxylic acid.

Baeyer Villiger Oxidation Mechanism

Baeyer-Villiger Monooxygenase

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Asymmetric oxidations play an important role in organic synthesis. Many valuable highly efficient chemocatalytic methods have been developed. Besides chemocatalysts, enzymes turned out to present useful catalysts. Notably a broad range of different types of oxidation reactions can be catalyzed by bio catalysts.

To start with the oxidation of a carbon atom, one can convert a ketone moiety into an ester in an asymmetric fashion by means of a so called Baeyer-Villiger monooxygenase.

Baeyer-Villiger Monooxygenase

Examples

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Baeyer-Villiger oxidation of a Mannich base having an appropriate substituent for selective migration on to the oxo carbonyl group opens a valuable possibility for the synthesis of $\beta$-amino esters and acids. Examples are the synthesis of epi-cytoxazone and the $\alpha$-hydroxy-$\beta$-amino acid derivatives from ketones respectively.

Baeyer Villiger Oxidation Example

Application

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  1. The Baeyer-Villiger reaction is widely appreciated in organic synthesis as it is applicable to a broad range of carbonylic compounds while the moiety that will migrate during the reaction can also be predicted to some extent.
  2. An additional attractive feature of the Baeyer-Villiger reaction is that the migrating group will typically retain its configuaration. This allows effective and selective oxidation reactions. However, a major drawback of the reaction is the intrinsic need for a potent and therefore hazardous oxidising agent.
  3. The classical approach to perform a Baeyer-Villiger reaction includes the use of organic peroxyacids as catalyst. In addition to the fact that these reactive compounds have to be handled with care, they are also relatively expensive.