Issue 18, 2009
From the journal:

Chemical Communications

Nucleophile-dependent regioselective ring opening of 2-substituted N,N-dibenzylaziridinium ions: bromideversushydride

Sae Young Yun,a   Saron Catak,b   Won Koo Lee,*a   Matthias D’hooghe,c   Norbert De Kimpe,c   Veronique Van Speybroeck,b   Michel Waroquier,b   Yongeun Kimd  and  Hyun-Joon Ha*d  

* Corresponding authors

a Department of Chemistry and Interdisciplinary Program of Integrated Biotechnology, Sogang University, Seoul, Korea

b Center for Molecular Modeling, Ghent University, Proeftuinstraat 86, Ghent, Belgium

c Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, Ghent, Belgium

d Department of Chemistry and Protein Research Center for Bio-Industry, Hankuk University of Foreign Studies, Yongin, Korea

Abstract

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.

Graphical abstract: Nucleophile-dependent regioselective ring opening of 2-substituted N,N-dibenzylaziridinium ions: bromideversushydride

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Article information

DOI
https://doi.org/10.1039/B822763B
Article type
Communication
Submitted
17 Dec 2008
Accepted
11 Mar 2009
First published
01 Apr 2009

Chem. Commun., 2009, 2508-2510

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Nucleophile-dependent regioselective ring opening of 2-substituted N,N-dibenzylaziridinium ions: bromideversushydride

S. Y. Yun, S. Catak, W. K. Lee, M. D’hooghe, N. De Kimpe, V. Van Speybroeck, M. Waroquier, Y. Kim and H. Ha, Chem. Commun., 2009, 2508 DOI: 10.1039/B822763B

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