Synthesis of terpene derivatives of ethanolamine using telomerization reaction

[Display omitted] •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. 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 2equiv 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.