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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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Article information


Submitted
02 Oct 2013
Accepted
30 Oct 2013
First published
31 Oct 2013

Chem. Commun., 2014,50, 1101-1103
Article type
Communication

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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