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Review | Regular issue | Vol 57, No. 8, 2002, pp.1525-1538
Published online, 1st January, 1970
DOI: 10.3987/REV-02-550
Synthetic Applications of Lewis Acid-Induced N-Methyleneamine Equivalents

Hyun-Joon Ha* and Won Koo Lee*

*Department of Chemistry, Hankuk University of Foreign Studies, Yongin, Kyunggi-Do, 449-791, Korea

Abstract

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 α-position of amines. Lewis acid-induced N-methyleneanilines can also serve as azadienes with electronrich diene for reverse electron demand [4π+2π] cycloaddition reactions.