Synthesis of terpene derivatives of ethanolamine using telomerization reaction. Issue 3 (20th January 2016)

• Record Type: Journal Article
• Authors: Zahreddine, Wissam; Lelong, Quentin; Karamé, Iyad; Kanj, Ali; Pinel, Catherine; Djakovitch, Laurent; Rataboul, Franck
• Is Part Of: Tetrahedron letters. Volume 57:Issue 3(2016)
• Page Start: 452
• Page End: 457
• Publication Date: 2016-01-20
• Subjects: Ethanolamine -- Isoprene -- Telomerization -- Palladium; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.12.075
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: New terpenoids have been prepared via telomerization of isoprene and ethanolamine. The reaction was catalyzed using PPh3 /Pd at 90 °C in methanol. The selectivity of mono and ditelomer families depended on reagent stoichiometry. The monotelomer family was composed of 6 isomers. Abstract: This Letter describes novel families of terpene derivatives bearing amino and alcohol functions, synthetically obtained through the telomerization of ethanolamine with isoprene. This reaction was performed at 90 °C in methanol and catalyzed by a Pd/PPh3 system. Four different product families were obtained depending on the telomerization degree with a total yield upto 85%. Monotelomers and ditelomers have been found to form preferentially. A variation of reagent stoichiometry allowed the tuning of the monotelomer and ditelomer selectivities within a 50–80% and 20–50% range, respectively. The best compromise total yield/monotelomer selectivity was obtained with 2 equiv of isoprene per ethanolamine. Deep analysis by NMR spectroscopy indicated that the monotelomer family was composed of 6 isomers, the main isomer possessing a tail-to-head trans configuration with a selectivity of 32.5% among all monotelomers.