A short isoprenylation protocol starting from non‐conjugated N‐Boc‐N‐(1,1‐dimethylallyl)hydrazones was developed utilising Thomson's traceless bond construction. This type of [3,3]‐sigmatropic rearrangement is catalysed by the Brønsted acid triflimide and liberates only gaseous by‐products. The required N‐Boc‐N‐allylhydrazine precursor is available in three steps starting from a known diazene using biocatalytic aldol addition and Tebbe olefination as key steps. Allylhydrazones are prepared via condensation with appropriate aldehydes. Scope and limitations of the [3,3]‐sigmatropic rearrangements are analysed.