1217898-68-4Relevant academic research and scientific papers
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
Fernández-Salas, José A.,Rodríguez-Fernández, M. Mercedes,Maestro, M. Carmen,García-Ruano, José L.
supporting information, p. 6046 - 6048 (2014/05/20)
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. the Partner Organisations 2014.
Asymmetric synthesis of 1,3-diamines by diastereoselective reduction of enantiopure n-tert-butanesulfinylketimines: unusual directing effects of the ortho-substituent
Martjuga, Marina,Shabashov, Dmitry,Belyakov, Sergey,Liepinsh, Edvards,Suna, Edgars
experimental part, p. 2357 - 2368 (2010/07/02)
(Figure Presented) Chiral, nonracemic 1,3-diamines were prepared in a highly diastereoselective reduction of diaryl N-tert-butanesulfinylketimines. Correlation between facial selectivity of the reduction and E or Z geometry of the starting ketimines suggests involvement of a cyclic transition state for the reduction. The ortho-substituent controls the geometry of N-tert- butanesulfinylketimines in the solid state and provides additional stabilization of the cyclic transition state.
