Ankita Biswas, Ananda Shankar Mondal, Ayan Chatterjee, Subhas Chandra Debnath, Saumen Hajra
A mechanochemical, solvent- and catalyst-free amination of chiral spiroaziridine oxindoles with alkyl amines is reported. The strain-release ring-opening process affords valuable 3-aminomethyl-3-alkylamino oxindoles in excellent yields with nearly complete transfer of chirality. Mechanochemical activation significantly improves stereochemical fidelity compared to solution-phase methods, highlighting an unusual role for mechanical force in controlling stereospecific reaction pathways.