One pot synthesis of aminohydroxylated triglycerides under aqueous biphasic conditions

Abstract

Herein is reported the one pot cascade hydroaminomethylation (HAM)/hydrohydroxymethylation (HHM) of triolein (T) using hydroformylating and hydrogenating Rh-catalysts stabilized by both phosphanes and amines under aqueous biphasic conditions. While T are mainly functionalized by N,N′-dialkylaminomethyl groups in organic solvents, they are predominantly functionalized by hydroxymethyl groups under aqueous biphasic conditions. The change in chemoselectivity is a consequence of both the displacement of the enamine-aldehyde equilibrium upon addition of water, and the partition of Rh-catalysts between the organic and the aqueous phases.