Bifunctional thiourea-modified polymers of intrinsic microporosity for enantioselective α-amination of 3-aryl-2-oxindoles in batch and flow conditions

Two novel polymers of intrinsic microporosity decorated with chiral thioureas have been used as recoverable organocatalysts in enantioselective α-amination of 3-aryl-substituted oxindoles, creating a quaternary stereocenter. Both catalysts were able to promote the reaction in excellent yields and good enantioselection. Catalyst II , with a pyridyl nucleus, was used in recycling experiments maintaining the activity without additional reactivation, and in flow processes allowing the synthesis of the amination product in multigram scale. A multigram scale preparation of enantioenriched 3-aryl-3-amino-2-oxindoles promoted by a novel chiral bifunctional thiourea, readily prepared from polymers of intrinsic microporosity.