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Issue 9, 2014
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Enantioselective synthesis of diaryl aziridines using tetrahydrothiophene-based chiral sulfides as organocatalysts

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Abstract

This work describes catalytic and asymmetric aziridinations (15 examples, 95–98% ee) of benzyl bromide and imines via the imino Corey–Chaykovsky reaction using (thiolan-2-yl)diarylmethanol benzyl ether as an organocatalyst. The catalyst and analogues thereof were prepared through an expeditious and efficient synthetic route featuring a double nucleophilic substitution and Shi epoxidation as key steps.

Graphical abstract: Enantioselective synthesis of diaryl aziridines using tetrahydrothiophene-based chiral sulfides as organocatalysts

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Publication details

The article was received on 02 Oct 2013, accepted on 30 Oct 2013 and first published on 31 Oct 2013


Article type: Communication
DOI: 10.1039/C3CC47550F
Citation: Chem. Commun., 2014,50, 1101-1103
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    Enantioselective synthesis of diaryl aziridines using tetrahydrothiophene-based chiral sulfides as organocatalysts

    M. Huang, H. Wu and R. Chein, Chem. Commun., 2014, 50, 1101
    DOI: 10.1039/C3CC47550F

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