Hydroaminomethylation of fatty acids with primary and secondary amines - Anew route to interesting surfactant substrates

The rhodium catalysed hydroaminomethylation of the unsaturated fatty acid d erivatives oleic acid ethyl ester (1) and oleyl alcohol (2) with the primar y amines hexylamine (3), benzylamine (4), aspartic acid diethyl ester (5) a nd valinol (6), and with the secondary amine morpholine (7), respectively, proceeds with good to excellent yields. Using primary amines the structure of the reaction products depends on the stoichiometry of the reactants. Per forming the reaction of (1) with (3) with an excess of the amine compound t he corresponding secondary amine (9) (1:1-adduct) was observed. Working wit h a 2-fold excess of (1) the tertiary amine (16) (2:1-adduct) was the main product.