Lead(IV) acetate oxidative ring-opening of 2,3-epoxy primary alcohols: a new entry to optically active α-hydroxy carbonyl compounds

Enrique Alvarez-Manzaneda,Rachid Chahboun,Esteban Alvarez,Ramón Alvarez-Manzaneda,Pedro E Muñoz,Fermín Jiménez,Hanane Bouanou

doi:10.1016/j.tetlet.2011.05.116

Lead(IV) acetate oxidative ring-opening of 2,3-epoxy primary alcohols: a new entry to optically active α-hydroxy carbonyl compounds

Enrique Alvarez-Manzaneda, Rachid Chahboun + Show 5 more

https://doi.org/10.1016/j.tetlet.2011.05.116

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Journal: Tetrahedron Letters	Publication Date: Jun 1, 2011
Citations: 10

Affiliation: University of Granada, University of Almería

#lead(IV) Acetate #Α-acetoxy Ketones + Show 8 more

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Abstract

The treatment of 2,3-epoxy primary alcohols with lead(IV) acetate (LTA) leads to α-acetoxy aldehydes or α-acetoxy ketones, through the nucleophilic ring-opening of an intermediate oxonium and the subsequent carbon–carbon bond cleavage. This reaction represents a new route to optically active α-hydroxy carbonyl compounds.

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