Lead(IV) acetate mediated cleavage of [beta]-hydroxy ethers: enantioselective synthesis of [alpha]-acetoxy carbonyl compounds

[alpha]-Acetoxy aldehydes or [alpha]-acetoxy ketones can be efficiently synthesized by treating 2,3-epoxy primary alcohols with lead tetraacetate. The reaction, which proceeds with complete regio- and stereoselectivity facilitates the enantioselective synthesis of [alpha]-acetoxy carbonyl compounds...

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Bibliographic Details
Published in:Tetrahedron 2011-11, Vol.67 (46), p.8910-8917
Main Authors: Alvarez-Manzaneda, Enrique, Chahboun, Rachid, Alvarez, Esteban, Alvarez-Manzaneda, Ramon, Munoz, Pedro E, Jimenez, Fermin, Bouanou, Hanane
Format: Article
Language:English
Subjects:
Alcohols
Carbonyl compounds
Cleavage
Ethers
Ketones
Oxygenated
Synthesis (chemistry)
Tetrahedrons
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Summary:[alpha]-Acetoxy aldehydes or [alpha]-acetoxy ketones can be efficiently synthesized by treating 2,3-epoxy primary alcohols with lead tetraacetate. The reaction, which proceeds with complete regio- and stereoselectivity facilitates the enantioselective synthesis of [alpha]-acetoxy carbonyl compounds from allyl alcohols, via Sharpless epoxidation. Cyclic [beta]-hydroxy ethers, with an oxygenated five-, six- or seven-membered ring, are transformed into [alpha]-acetoxy ethers.
ISSN:0040-4020
DOI:10.1016/j.tet.2011.09.056