A new synthetic approach towards N-alkylated 2-epi-valienamines via palladium-catalyzed coupling reaction

Preparation of N-alkylated 2-epi-valienamines was accomplished by the palladium-catalyzed coupling reaction of the allylic chloride 5 with various amines in the presence of trimethylolpropane phosphite (TMPP). The 2-epi-valienamine precursor (i.e. allylic chloride 5) was obtained from the reaction of diol 2 with Vieheʹs salt and the diol 2 was readily prepared from (−)-quinic acid in 10 steps.