Iodotrimethylsilane-promoted 1, 4-addition of copper acetylides to α, β-unsaturated ketones and aldehydes

M Eriksson, T Iliefski, M Nilsson…

Index: Eriksson, Magnus; Iliefski, Tommy; Nilsson, Martin; Olsson, Thomas Journal of Organic Chemistry, 1997 , vol. 62, # 1 p. 182 - 187

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Citation Number: 56

Abstract

In the presence of iodotrimethylsilane (TMSI) and lithium iodide in tetrahydrofuran, the otherwise unreactive copper acetylides add to enones present as s-trans conformers to provide good yields of the silyl enol ethers of β-acetylido carbonyl compounds. Typically good substrates are 2-cyclopentenone, 2-cyclohexenone, α, β-unsaturated aldehydes, and β-alkoxy-α-enones. Copper acetylide reagents prepared from CuI and an alkynyllithium ...