Abstract
Copper-catalyzed skeletal rearrangement of <i>O</i>-propargylic aryloximes (<i>E</i>)-<b>1</b> were carried out to afford the corresponding four-membered cyclic nitrones <b>2</b> in good to excellent yields. The optimal reactions conditions of the highly regioselective reactions involved the use of [CuCl(cod)]<sub>2</sub> in acetonitrile at 70 °C. In the case of (<i>Z</i>)-<b>1</b>, however, the reaction proceeded in the absence of the copper catalysts to afford the identical compound <b>2</b> in good yields. Furthermore, the reactions were also carried out using chiral substrates (<i>R</i>)-<b>1</b> in the presence of Cu catalysts to afford (<i>R</i>)-<b>2</b> with good levels of chirality transfer.
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