Enantioselective catalysis for agrochemicals: Synthetic routes to (S)-metolachlor, (R)-metalaxyl and (αS, 3R)-clozylacon

The application of enantioselective catalytic methods for the technical preparation of chiral agrochemicals is illustrated for three active ingredients of the acylanilide type. The key step for the technical synthesis of the herbicide (S)-metolachlor is the enantioselective hydrogenation of an imine intermediate using a novel iridium ferrocenyldiphosphine catalyst with an unprecedented high activity and 80% ee. (R)-metalaxyl and (αS,3R)-clozylacon were synthesized via the enantioselective hydrogenation of corre-sponding enamide precursors with Rh and Ru/binap catalysts with >95% and 99% enantiomeric purity, respectively. © 1998 Society of Chemical Industry