Catalytically generated N-methyleneamine equivalents from Nmethoxymethylanilines, 1,3,5-triphenyl-and 1,3,5-tribenzylhexahydro-1,3,5triazines in the presence of Lewis acid reacted with 2-trimethylsilyloxyfuran to give 5-aminomethyl-2.5-dihydmfuran-2-ones in high yield.The Mannich reaction as a method introducing nucleophiles at a-position of mines has been widely employed in synthetic chemistry?However, the traditional methods have some drawbacks.The reaction prevents use of compounds with acid sensitive functionalities due to the harsh reaction conditions with iminium ions in acidic pmtic system.Aminomethylation can not be achieved through the classical method of Mannich reaction.Moreover, one of the simplest imine (monomeric formaldehyde imine) of Nmethyleneamine for aminomethylation is limited from a synthetic viewpoint because it is difficult to generate the N-methyleneamine, which is only h o w n in gas phase through flash vacuum them0l~sis.3Methods for the preparation of N-methyleneamine in situ for synthetic purpose have been devised by treating N-methoxymethylamines4 or N-~yanometh~laminess with alkyllithium for the synthesis of N-asubstituted methylamines and p-lactams.Other aminomethylation reactions with silyl enol ethers have also been reported to be achieved from N-alkoxymethylamines catalyzed by iodotrimethylsilane,6 from
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Ha et al. (1997) studied this question.