Tetrahedron

SmI 2-Mediated 3-exo-trig cyclisation of δ-oxo-α, β-unsaturated esters to cyclopropanols and derivatives

S Bezzenine-Lafollée, F Guibé, H Villar, R Zriba

Index: Bezzenine-Lafollee, Sophie; Guibe, Francois; Villar, Helene; Zriba, Riadh Tetrahedron, 2004 , vol. 60, # 32 p. 6931 - 6944

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Citation Number: 26

Abstract

In the presence of samarium diiodide and a proton source, δ-oxo-γ, γ-disubstituted-α, β- unsaturated esters of general formula R–CO–C (R′, R′)–CH CH–CO2Bn readily cyclise to trans-cyclopropanol products and/or lactones derived from the cis isomers. For R= aryl, good stereoselectivities (ca 90%) in favor of the alcohols are generally obtained while a mixture of alcohols and lactones is obtained with R= alkyl or H. For R= cyclopropyl, the ...