Heterocyclic Trost's ligands. Synthesis and applications in asymmetric allylic alkylation

Abstract

Condensation (1R,2R)-1,2-diaminocyclohexane with 2-(diphenylphosphino) nicotinic acid and 3-(diphenylphosphino)quinoxaline-2-carboxylic acid afforded the corresponding diphosphines. These ligands were used in the palladium-catalyzed alkylation of various allylic acetates with carbon and nitrogen nucleophiles, giving generally lower enantioselectivities than the analogous non-heterocyclic ligands.