Tetrahedron letters

Nitroalkanes and ethyl glyoxalate as common precursors for the preparation of both β-keto esters and α, β-unsaturated esters

R Ballini, D Fiorini, A Palmieri

Index: Ballini, Roberto; Fiorini, Dennis; Palmieri, Alessandro Tetrahedron Letters, 2004 , vol. 45, # 38 p. 7027 - 7029

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Citation Number: 39

Abstract

β-Nitro acrylic esters, obtained by the reaction of nitroalkanes and ethyl glyoxalate, are the key building blocks for the immediate synthesis of both the title compounds. In fact, their treatment with titanium trichloride produce the direct conversion to the β-keto esters, while their reaction with sodium boron hydride gives the one-pot synthesis of α, β-unsaturated esters through formal substitution of the vinylic nitro group with an hydrogen.

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