Hydroaminomethylation of fatty acids with primary and secondary amines — A new route to interesting surfactant substrates

Abstract

The rhodium catalysed hydroaminomethylation of the unsaturated fatty acid derivatives oleic acid ethyl ester (1) and oleyl alcohol (2) with the primary amines hexylamine (3), benzylamine (4), aspartic acid diethyl ester (5) and 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. Performing the reaction of (1) with (3) with an excess of the amine compound the corresponding secondary amine (9) (1:1-adduct) was observed. Working with a 2-fold excess of (1) the tertiary amine (16) (2:1-adduct) was the main product.