Synthesis of terpene derivatives of ethanolamine using telomerization reaction

Wissam Zahreddine , Quentin Lelong (1) , Iyad Karame (1) , Ali Kanj , C. Pinel (2) , L. Djakovitch (2) , F. Rataboul (2)

1 IRCELYON - Institut de recherches sur la catalyse et l'environnement de Lyon
2 CDURABLE - IRCELYON-C'Durable

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 degrees 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 mono-telomer 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. (C) 2015 Elsevier Ltd. All rights reserved.

Domaines: Catalyse; Environnement et Société

Wissam Zahreddine, Quentin Lelong, Iyad Karame, Ali Kanj, C. Pinel, et al.. Synthesis of terpene derivatives of ethanolamine using telomerization reaction. Tetrahedron Letters, 2016, 57 (3), pp.452-457. ⟨10.1016/j.tetlet.2015.12.075⟩. ⟨hal-01293108⟩