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

Intramolecular homolytic substitution (S(H)i) 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-benz...

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 50; no. 45; pp. 6046 - 6048
Main Authors Fernandez-Salas, Jose A., Mercedes Rodriguez-Fernandez, M., Carmen Maestro, M., Garcia-Ruano, Jose L.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2014
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
SULTAM AUXILIARIES
BENZOSULTAMS
ASYMMETRIC-SYNTHESIS
SULFINAMIDES
INTRAMOLECULAR HOMOLYTIC SUBSTITUTION
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Summary:Intramolecular homolytic substitution (S(H)i) 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.
ISSN:1359-7345
1364-548X
DOI:10.1039/c4cc01831a