Synthesis of terpene derivatives of ethanolamine using telomerization reaction

SSCI-VIDE+CDFA+QLE:IKA:CPI:LDJ:FRA; International audience; This Letter describes novel families of terpene derivatives bearing amino and alcohol functions, synthetically obtained through thetelomerization of ethanolamine with isoprene. This reaction wasperformed at 90 degrees C in methanol and catalyzed by a Pd/PPh3 system.Four different product families were obtained depending on thetelomerization degree with a total yield upto 85%. Monotelomers andditelomers have been found to form preferentially. A variation ofreagent stoichiometry allowed the tuning of the mono-telomer andditelomer selectivities within a 50-80% and 20-50% range, respectively.The best compromise total yield/monotelomer selectivity was obtainedwith 2 equiv of isoprene per ethanolamine. Deep analysis by NMRspectroscopy indicated that the monotelomer family was composed of 6isomers, the main isomer possessing a tail-to-head trans configurationwith a selectivity of 32.5% among all monotelomers. (C) 2015 ElsevierLtd. All rights reserved.