biostudies-literatureUnknown2(4)Keenan TA highly efficient, cost-effective, and environmentally friendly protocol is reported for the C5-selective alkylation of hydantoins under phase-transfer catalysis. The reactions are scalable and only require a catalytic amount of tetrabutylammonium bromide (TBAB) to achieve high yields under mild reaction conditions. Moreover, the method is applicable to a wide range of electrophiles, including alkyl-, allyl-, propargyl-, and benzyl halides, as well as acrylates and dibromoalkanes, but also to virtually any hydantoin precursor. We also highlight the potential for an enantioselective adaptation using a chiral phase-transfer catalyst.ACS organic & inorganic Au312-317https://www.ebi.ac.uk/biostudies/studies/S-EPMC9954259biostudies-literaturePhase-Transfer-Catalyzed Alkylation of Hydantoins.PMC9954259Keenan TJean AArseniyadis SfalsePhase-Transfer-Catalyzed Alkylation of Hydantoins.A highly efficient, cost-effective, and environmentally friendly protocol is reported for the C5-selective alkylation of hydantoins under phase-transfer catalysis. The reactions are scalable and only require a catalytic amount of tetrabutylammonium bromide (TBAB) to achieve high yields under mild reaction conditions. Moreover, the method is applicable to a wide range of electrophiles, including alkyl-, allyl-, propargyl-, and benzyl halides, as well as acrylates and dibromoalkanes, but also to virtually any hydantoin precursor. We also highlight the potential for an enantioselective adaptation using a chiral phase-transfer catalyst.2022-01-01T00:00:00Z2022 Aug2025-04-26T10:20:07.247Z2025-04-06T13:17:38.46ZS-EPMC99542593685558910.1021/acsorginorgau.1c00058