pi-Allylic C1-substitution in water with nitromethane using amphiphilic resin-supported palladium complexes.

Nitromethane was safely applied as a C1 nucleophile for palladium-catalyzed pi-allylic substitution in water with amphiphilic PS-PEG resin-supported phosphine-palladium complexes. Catalytic asymmetric nitromethylation of cycloalkenyl esters was achieved in water as a single reaction medium under heterogeneous conditions using 5 mol % palladium of a PS-PEG resin-supported palladium-imidazoindolephosphine complex to give optically active (cycloalkenyl)nitromethanes with up to 98% ee.