Nucleophile-dependent regioselective ring opening of 2-substituted N,N-dibenzylaziridinium ions: bromide versus hydride

被引：38

作者：

Yun, Sae Young ^{[1
,2
]}

Catak, Saron ^{[3
]}

Lee, Won Koo ^{[1
,2
]}

D'hooghe, Matthias ^{[4
]}

De Kimpe, Norbert ^{[4
]}

Van Speybroeck, Veronique ^{[3
]}

Waroquier, Michel ^{[3
]}

Kim, Yongeun ^{[5
,6
]}

Ha, Hyun-Joon ^{[5
,6
]}

机构：

[1] Sogang Univ, Dept Chem, Seoul 121742, South Korea

[2] Sogang Univ, Interdisciplinary Program Integrated Biotechnol, Seoul 121742, South Korea

[3] Univ Ghent, Ctr Mol Modeling, B-9000 Ghent, Belgium

[4] Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium

[5] Hankuk Univ Foreign Studies, Dept Chem, Yongin 449791, South Korea

[6] Hankuk Univ Foreign Studies, Prot Res Ctr Bioind, Yongin 449791, South Korea

来源：

CHEMICAL COMMUNICATIONS | 2009年 / 18期

基金：

新加坡国家研究基金会;

关键词：

SUBSTITUTION REACTIONS; AZIRIDINIUM IONS; AMINES; DENSITY; SALTS; 2-(CYANOMETHYL)AZIRIDINES; THERMOCHEMISTRY; REACTIVITY; FLUORIDE;

D O I：

10.1039/b822763b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The ring opening of 2-substituted N,N-dibenzylaziridinium ions by bromide exclusively occurs at the substituted aziridine carbon atom in a stereospecific way, whereas the opposite regioselectivity was observed for hydride-induced ring opening at the unsubstituted position; furthermore, this unprecedented hydride-promoted reactivity was validated by means of Density Functional Theory (DFT) calculations.

引用

页码：2508 / 2510

页数：3

共 4 条

[1] Regioselective Ring Opening Reactions of Pyridine N-Oxide Analogues by Magnesium Hydride Complexes
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[3] B2(OH)4-Mediated Reductive Ring-Opening of N-Tosyl Aziridines by Nitroarenes: A Green and Regioselective Access to Vicinal Diamines
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[4] An efficient synthetic route to substituted tetrahydropyrimidines by Cu(OTf)O2-mediated nucleophilic ring-opening followed by the [4+2] cycloaddition of N-tosylazetidines with nitriles
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TETRAHEDRON LETTERS, 2009, 50 (10) : 1105 - 1109

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