Ganem oxidation
| Ganem oxidation | |
|---|---|
| Named after | Bruce Ganem |
| Reaction type | Organic redox reaction |
In
Mechanism
As in other oxoammonium-catalyzed oxidation reactions, the negatively charged oxygen atom of the trialkylamine N-oxide molecule attacks the alkyl halide in a SN2 manner, kicking of the halide as a leaving group. A trialkylamine deprotonates the α-carbon atom, the resulting electron pair shifts onto the oxygen atom, which shifts its own excess electron pair onto the nitrogen atom. This generates the desired carbonyl, as well as the aforementioned trialkylamine. The reaction is an enhancement of the Kornblum oxidation protocol, which was originally developed using dimethyl sulfoxide or pyridine-N-oxide as the nucleophile.
Applications
The Ganem oxidation has been used as an intermediate step in the total synthesis of (−)-okilactomycin, converting a primary alkyl halide into an aldehyde.[2]
References
- .
- PMID 17997560.
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