Phase-Transfer-Catalyzed Alkylation of Hydantoins

被引：13

作者：

Keenan, Thomas ^{[1
]}

Jean, Alexandre ^{[2
]}

Arseniyadis, Stellios ^{[1
]}

机构：

[1] Queen Mary Univ London, Dept Chem, London E1 4NS, England

[2] Ctr Ind Res, Oril Ind, F-76210 Bolbec, France

来源：

ACS ORGANIC & INORGANIC AU | 2022年 / 2卷 / 04期

关键词：

phase-transfer catalysis; hydantoins; alkylation; allylation; propargylation; Michael addition; ALPHA-AMINO; DERIVATIVES; CHEMISTRY; ARYLATION;

D O I：

10.1021/acsorginorgau.1c00058

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

收藏

页码：312 / 317

页数：6

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