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A Remarkably Efficient Phase-Transfer Catalyzed Amination of α-Bromo-α, β-Unsaturated Ketones in Water
Heteroatom Chemistry ( IF 0.3 ) Pub Date : 2021-01-04 , DOI: 10.1155/2021/6616458
Alemayehu Mekonnen 1 , Alemu Tesfaye 1
Affiliation  

Tandem conjugate addition–alkylation reaction of various amines with α-bromo-α, β-unsaturated ketones resulted in near-quantitative conversions into the corresponding aziridines when the reaction was carried out in the presence of 10 mol% of phase-transfer, PT catalysts in water. Some chiral quaternary ammonium salts derived from Cinchona alkaloids were investigated as water-stable PT catalysts. The scope and limitations of the reaction have also been investigated. The catalytic performances were significantly improved in comparison with the corresponding ordinary quaternary ammonium salt catalysts, and excellent yields (81%–96%) were obtained. Although an increase in the rate of aziridination has been accomplished, no stereoselectivity was observed. The positive values of the protocol have been confirmed.

中文翻译:

水中α-溴-α,β-不饱和酮的高效相转移催化胺化

当在10 mol%的相转移PT催化剂存在下进行反应时,各种胺与α-β-不饱和酮的串联共轭加成-烷基化反应可将近定量转化为相应的氮丙啶在水里。金鸡纳衍生的一些手性季铵盐研究了生物碱作为水稳定的PT催化剂。还研究了反应的范围和局限性。与相应的普通季铵盐催化剂相比,其催化性能得到了显着改善,并获得了优异的收率(81%–96%)。尽管已经完成了叠氮化率的提高,但是没有观察到立体选择性。该协议的正值已得到确认。
更新日期:2021-01-04
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