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Heerdegen, Desirée; Junker, Julia; Dittrich, Sebastian; Mayer, Peter; Bracher, Franz ORCID: 0000-0003-0009-8629 (2020): Traceless Isoprenylation of Aldehydes via N‐Boc‐N‐(1,1‐dimethylallyl)hydrazones. In: European Journal of Organic Chemistry, Vol. 2020, No. 24: pp. 3680-3687
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Abstract

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.