Stereochemical aspects and the synthetic scope of the S(H)i 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

Stereochemical aspects and the synthetic scope of the S(H)i at the sulfur atom. Preparation of enantiopure 3-substituted 2,3-dihydro-1,2-benzoisothiazole 1-oxides and 1,1-dioxides

Chem Commun (Camb). 2014 Jun 7;50(45):6046-8. doi: 10.1039/c4cc01831a. Epub 2014 Apr 28.

Authors

José A Fernández-Salas¹, M Mercedes Rodríguez-Fernández, M Carmen Maestro, José L García-Ruano

Affiliation

¹ Departamento de Química Orgánica, Universidad Autónoma de Madrid, 28049-Cantoblanco, Madrid, Spain. mercedes.rodriguez@uam.es carmen.maestro@uam.es.

PMID: 24769863
DOI: 10.1039/c4cc01831a

Abstract

Intramolecular homolytic substitution (SHi) 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.