| Abstract
| - N-(Trialkylsilyl)allylamines can be deprotonated at the cis-vinylic position to yield 3,N-dilithio-N-(trialkylsilyl)allylamines under mild conditions. N-(Trialkylsilyl)allylamines with terminal alkylsubstituents were reported not to form dianions under the same conditions. During our investigations we found that N-(tert-butyldimethylsilyl)-2-buten-1-amine (1) is deprotonated under thereaction conditions reported in the literature, but the resulting dianion is quenched by etherealsolvents. Consequently, new reaction conditions were developed that allow the generation of stabledianions from allylamines with terminal alkyl substituents. Thus, 2,3-disubstituted pyrroles hithertounattainable via this methodology were formed from 3,N-dilithio-N-(tert-butyldimethylsilyl)-2-buten-1-amine (2) and various carbonyl electrophiles in good yields.
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