Issue 17, 2006
From the journal:

Chemical Communications

Direct synthesis of chiral aziridines from N-tert-butyl-sulfinylketimines

Daniel Morton,a   David Pearson,†b   Robert A. Fielda  and  Robert A. Stockman*a  

* Corresponding authors

a School of Chemical Sciences and Pharmacy, University of East Anglia, Norwich, UK
E-mail: r.stockman@uea.ac.uk

b Millennium Pharmaceuticals, Granta Park, Great Abington, Cambridge, UK

Abstract

The direct preparation of a range of variously substituted chiral tert-butylsulfinylketimines was achieved in good yield (41–90%), with relatively rapid reaction times (4–15 hours); their synthetic application was examined through the reaction with the ylides derived from trimethylsulfonium iodide and S-allyl tetrahydrothiophenium bromide, affording convenient access to a diverse range of highly substituted chiral aziridines in up to 78% yield and > 90% d.e.

Graphical abstract: Direct synthesis of chiral aziridines from N-tert-butyl-sulfinylketimines

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Article information

DOI
https://doi.org/10.1039/B601527A
Article type
Communication
Submitted
01 Feb 2006
Accepted
16 Mar 2006
First published
27 Mar 2006

Chem. Commun., 2006, 1833-1835

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Direct synthesis of chiral aziridines from N-tert-butyl-sulfinylketimines

D. Morton, D. Pearson, R. A. Field and R. A. Stockman, Chem. Commun., 2006, 1833 DOI: 10.1039/B601527A

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