Lead(IV) acetate mediated cleavage of β-hydroxy ethers: enantioselective synthesis of α-acetoxy carbonyl compounds
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Alvarez-Manzaneda, Enrique; Chahboun, Rachid; Alvarez, Esteban; Alvarez-Manzaneda Roldán, Ramón Jesús; Muñoz, Pedro E.; [et al.]Fecha
2011-09-14Resumen
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.
Palabra/s clave
Hydroxycarbonyl compounds
Allyl alcohols
Asymmetric synthesis
Lead tetraacetate
Hydroxy ethers