Phase-Transfer-Catalyzed Alkylation of Hydantoins

ACS Org Inorg Au. 2022 Feb 9;2(4):312-317. doi: 10.1021/acsorginorgau.1c00058. eCollection 2022 Aug 3.


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.

PMID:36855589 | PMC:PMC9954259 | DOI:10.1021/acsorginorgau.1c00058


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