Safety Asymmetric π-Allylic C1-Substitution with Nitromethane in Water

Significance

Catalytic π-allylic nitromethylations of cycloalkenyl esters were achieved in water as a single reaction medium under heterogeneous conditions using PS-PEG resin-supported palladium complexes. Thus, methyl cyclohexenyl carbo­nates 1a-e react with 3 equivalents of nitromethane in an aqueous Li₂CO₃ solution in the presence of 5 mol% of an amphiphilic resin-supported palladium complex 3 at 60 °C for 12 h to give 76-93% isolated yields of the nitromethylated products 2a-e.