Lead(IV) acetate mediated cleavage of β-hydroxy ethers: enantioselective synthesis of α-acetoxy carbonyl compounds

α-Acetoxy aldehydes or α-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 α-acetoxy carbonyl compounds from allyl alcohol...

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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, Ramón, Muñoz, Pedro E., Jimenez, Fermín, Bouanou, Hanane
Format: Article
Language:English
Subjects:
Allyl alcohols
Asymmetric synthesis
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Hydroxy ethers
Hydroxycarbonyl compounds
Lead tetraacetate
Organic chemistry
Preparations and properties
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Summary:α-Acetoxy aldehydes or α-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 α-acetoxy carbonyl compounds from allyl alcohols, via Sharpless epoxidation. Cyclic β-hydroxy ethers, with an oxygenated five-, six- or seven-membered ring, are transformed into α-acetoxy ethers. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.09.056