Síntese verde de N-alquilcitroneliliminas e N-alquilcitronelilaminas a partir do (R)-Citronelal - Aplicação na Síntese de um Juvenóide

Abstract

We developed a method for selective synthesis of citronellylimines by reaction of (R)-citronellal with primary amines, under mild conditions and solvent-free environment. The reaction was performed by neutral Al2O3 as anhydrous drying agent and provided the respective aldimines with good to excellent yields. This protocol was extended to the chemoselective synthesis of citronellylamines through reductive amination one-pot, adding NaBH4 to the reaction medium. The methodology was successfully used in the synthesis of 3,7-dimethyl-N-(prop-2-ynyl) oct-6-en-1-amine, a juvenile hormone active against stablefly (Stomoxys calcitrans) and housefly (Musca domestica), directly from citronella oil. The use of microwaves accelerates the reaction. The method is simple, clean and general, being extended to other examples of aliphatic and aromatic aldehydes.