Traceless Isoprenylation of Aldehydes via N‐Boc‐N‐(1,1‐dimethylallyl)hydrazones

Heerdegen, Desirée; Junker, Julia; Dittrich, Sebastian; Mayer, Peter und Bracher, Franz (2020): Traceless Isoprenylation of Aldehydes via N‐Boc‐N‐(1,1‐dimethylallyl)hydrazones. In: European Journal of Organic Chemistry, Bd. 2020, Nr. 24: S. 3680-3687

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.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department für Pharmazie - Zentrum für Pharmaforschung
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie ; 600 Technik, Medizin, angewandte Wissenschaften > 610 Medizin und Gesundheit
• ISSN: 1099-0690
• Sprache: Englisch