15934-26-6Relevant academic research and scientific papers
Preparation of racemic and enantiopure arenesulfonimidoyl azoles - New compounds chiral on sulfur
Kluge, Ralph,Hocke, Heiko,Schulz, Manfred,Schilke, Frank
, p. 179 - 206 (2007/10/03)
The novel arenesulfonimidoyl imidazoles 7a-j and nitrotriazoles 9d-j were obtained in good yield from the corresponding arenesulfonimidoyl chlorides 6a-j. The reaction of optically pure sulfonimidoyl chlorides 6 with imidazole resulted in the first reported optically active arenesulfonimidoyl imidazoles 7 with high enantiomeric purities (ee up to >99%); the stereochemical course of the reaction (inversion or retention at sulfur) is shown to be strongly dependent on the aryl substituent. By contrast, the analogous reaction of optically pure compounds 6 with 3-nitro-1,2,4-triazole led to racemic arenesulfonimidoyl nitrotriazoles 9. Optically active compounds of this type, (S)-9f (ee 99%) and (R)-9f (ee 92%), were obtained by semi-preparative chiral HPLC. The optically active arenesulfonimidoyl imidazolium salt (RS,RC)-8j was prepared by diastereoselective methylation (de >90%) of the optically pure imidazole derivative (RS,RC)-7j.
