Stereochemical aspects and the synthetic scope of the SHi at the sulfur atom. Preparation of enantiopure 3-substituted 2,3-dihydro-1,2-benzoisothiazole 1-oxides and 1,1-dioxides

José A. Fernández-Salas; M. Mercedes Rodríguez-Fernández; M. Carmen Maestro; José L. García-Ruano

doi:10.1039/C4CC01831A

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Stereochemical aspects and the synthetic scope of the S_Hi at the sulfur atom. Preparation of enantiopure 3-substituted 2,3-dihydro-1,2-benzoisothiazole 1-oxides and 1,1-dioxides†

José A. Fernández-Salas,^a M. Mercedes Rodríguez-Fernández,*^a M. Carmen Maestro*^a and José L. García-Ruano^a

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* Corresponding authors

^a Departamento de Química Orgánica, Universidad Autónoma de Madrid, 28049-Cantoblanco, Madrid, Spain
E-mail: mercedes.rodriguez@uam.es, carmen.maestro@uam.es

Abstract

Intramolecular homolytic substitution (S_Hi) on the sulfur atom at acyclic N-(o-bromobenzyl)sulfinamides takes place with a complete inversion of the configuration and provides an excellent tool to connect N-tert-butanesulfinylimines with enantiopure 3-substituted benzo-fused sulfinamides (1,2-benzoisothiazoline 1-oxides) and the related pharmacologically relevant sulfonamides.

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DOI: https://doi.org/10.1039/C4CC01831A
Article type: Communication
Submitted: 11 Mar 2014
Accepted: 17 Apr 2014
First published: 22 Apr 2014

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Chem. Commun., 2014,50, 6046-6048

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Stereochemical aspects and the synthetic scope of the S_Hi at the sulfur atom. Preparation of enantiopure 3-substituted 2,3-dihydro-1,2-benzoisothiazole 1-oxides and 1,1-dioxides

J. A. Fernández-Salas, M. M. Rodríguez-Fernández, M. C. Maestro and J. L. García-Ruano, Chem. Commun., 2014, 50, 6046 DOI: 10.1039/C4CC01831A

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