Lewis acid induced N-methyleneamine equivalents. Part 3. Addition of allyl nucleophiles to TiCl4-induced N-methyleneamine equivalents: synthesis of 1,2,3,4-tetrahydroquinolines and homoallylic anilines

Abstract

TiCl₄-induced N-methyleneamine equivalents from N-(methoxymethyl)anilines or 1,3,5-triphenylhexahydro-1,3,5-triazines have been treated with allyltrimethylsilane to give a mixture of 1,2,3,4-tetrahydroquinolines and homoallylic anilines arising from branching reactions from the same cationic intermediate. Changing the allylic nucleophile to allylmagnesium bromide and allyltributyltin leads to the reaction proceeding in only one direction and the selective synthesis of homoallylic anilines without the formation of quinolines.