Generation of an <i>N</i>-Sodioazomethine Ylide and Its Cycloadditions with α,β-Unsaturated Esters

Abstract

Abstract Treatment of methyl 2-(benzylideneamino)propanoate with sodium hydride in THF generates an N-sodioazomethine ylide, which shows a very poor stereoselectivity in the cycloaddition with methyl acrylate. However, addition of such a base as triethylamine or t-butyl alcohol improves the selectivity. Chemical properties of the ylide have been discussed on the basis of the selectivity totally different from that of N-lithio analogue.