A new route to secondary amines from bis-(alkoxymethyl)-alkylamines - The activation of an aminomethyl group and protection of the product by the same functional group

Article abstract of DOI:10.1016/S0040-4039(00)97589-0

Treatment of N,N-bis(alkoxymethyl)alkylamines with a variety of acidic reagents affords good yields of N-alkoxymethyl-N-alkylmethyleneiminium salts which react with trimethylsilyl enol ethers, and nucleophilic aromatic substrates to form protected secondary amines or tertiary amines by domino reactions; silyl ketene acetals afford tertiary amines only.