Issue 11, 2008
From the journal:

Organic & Biomolecular Chemistry

Regio- and stereocontrolled synthesis of novel 3-sulfonamido-2,3,4,5-tetrahydro-1,5-benzothiazepines from 2-(bromomethyl)- or 2-(sulfonyloxymethyl)aziridines†

Michinori Karikomi,‡a   Matthias D'hooghe,a   Guido Verniesta  and  Norbert De Kimpe*a  

* Corresponding authors

a Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Belgium
E-mail: norbert.dekimpe@UGent.be
Fax: +32 9 264 6243
Tel: +32 9 264 5951

Abstract

2-(Bromomethyl)-1-sulfonylaziridines were converted into novel 3-sulfonamido-2,3,4,5-tetrahydro-1,5-benzothiazepines upon treatment with 2-aminothiophenol in THF in the presence of K2CO3. Starting from 3-substituted 2-(sulfonyloxymethyl)aziridines, a regio- and stereocontrolled synthesis of trans-2-phenyl- and trans-4-(phenyl or propyl)-3-sulfonamido-2,3,4,5-tetrahydro-1,5-benzothiazepines was developed in good yields via two different reaction pathways, depending on the nature of the sulfonyloxy group.

Graphical abstract: Regio- and stereocontrolled synthesis of novel 3-sulfonamido-2,3,4,5-tetrahydro-1,5-benzothiazepines from 2-(bromomethyl)- or 2-(sulfonyloxymethyl)aziridines

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Article information

DOI
https://doi.org/10.1039/B804246M
Article type
Communication
Submitted
11 Mar 2008
Accepted
12 Mar 2008
First published
16 Apr 2008

Org. Biomol. Chem., 2008,6, 1902-1904

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Regio- and stereocontrolled synthesis of novel 3-sulfonamido-2,3,4,5-tetrahydro-1,5-benzothiazepines from 2-(bromomethyl)- or 2-(sulfonyloxymethyl)aziridines

M. Karikomi, M. D'hooghe, G. Verniest and N. De Kimpe, Org. Biomol. Chem., 2008, 6, 1902 DOI: 10.1039/B804246M

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