A totally controlled regiodivergent azidation of activated N-allenamides is presented. Using TMSN₃/TBAF, β-azidation of N-allenamides occurs exclusively, yielding vinyl azides. Conversely, employing a TFA/TMSN₃ mixture results solely in the formation of γ-azides. A subsequent [1,3] azide shift of the latter with DBU produces α-amido vinyl azides. Additionally, δ-difluorinated azides featuring an ynamide are selectively synthesized from ene-ynamides. The practical applicability of these transformations is demonstrated through the formation of cyanide derivatives, trifluoromethyl ketones and primary enamines.

中文翻译：

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活化的 N-烯酰胺的区域选择性和立体选择性叠氮化：α、β、γ 和 δ-酰胺叠氮化物的入口


提出了活化的 N-烯酰胺的完全受控区域发散叠氮化。使用 TMSN₃/TBAF，N-烯酰胺的 β 叠氮化反应仅发生，产生乙烯基叠氮化物。相反，使用 TFA/TMSN₃ 混合物仅导致 γ-叠氮化物的形成。随后 [1,3] 后者与 DBU 的叠氮化物偏移产生α-酰胺基叠氮化物。此外，具有烯酰胺的 δ-二氟叠氮化物是从烯-酰胺选择性合成的。这些转化的实际适用性通过氰化物衍生物、三氟甲基酮和伯烯胺的形成来证明。