Aminosilylation of dimethyl acetylenedicarboxylate

Nucleophilic addition of N-trimethylsilylakylamines, Me3SiNHR (where R = and t-Bu), and bis(trimethylsilyl)amine to dimethyl acetylenedicarboxylate occurs via siliconnitrogen bond cleavage to give dimethyl 2-alkyl-(or trimethylsilyl-)amino-3-trimethylsilyl furmarates as the sole products. These are cleaved by methanol to yield dimethyl 2-(alkyl)aminofumarates. Tris(trimethylsilyl)amine does not react with dimethyl acetylenedicarboxylate.