Synthetic applications of Lewis acid-induced N-methyleneamine equivalents

초록

The reactions involving one of the simplest imines, N-methyleneamine (monomeric formaldehyde imine), are very limited from the synthetic viewpoint because it is difficult to generate the N-methyleneamine. In this review are summarized a method and synthetic applications of N-methyleneamine equivalents generated from hexahydro-1,3,5-triazines or N-methoxymethylamines in the presence of a Lewis acid. Reactions with various nucleophiles yield aminomethylated products at the alpha-position of amines. Lewis acid-induced N-methylencanilines can also serve as azadienes with electron rich diene for reverse electron demand [4pi+2pi] cycloaddition reactions.

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