N-silyloxaziridines: Synthesis and use for electrophilic amination

摘要

N-Silyloxaziridines were synthesized for the first time. Their tert-butyldiphenylsilyl (TBDPS) derivatives were stable reagents that were prepared on a multigram scale in three steps and in 44% overall yield from the corresponding benzylamines. They were mild electrophilic aminating reagents that reacted at room temperature with diversely substituted primary and secondary amines to produce N-monoalkyl or N,N-dialkyl benzaldehyde hydrazones in 44a-87% yield.