123552-90-9Relevant 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.
Synthesis, deprotonation, and alkylation of S-allyl sulfoximines
Harmata,Claassen II
, p. 6497 - 6500 (2007/10/02)
N-Phenyl-S-(4-methylphenyl)-sulfoximidoyl chloride 1 reacts with allyltrimethylsilane in the presence of aluminum chloride to give benzothiazine 4 in fair yield along with a small amount of S-allyl sulfoximine 3a. On the other hand, 1 reacts with allyltributyltin to give the S-allyl sulfoximine 3a almost exclusively. This latter reaction appears to be general. The sulfoximine 3a is thermally stable and can be deprotonated smoothly with n-BuLi. The anion reacts regioselectively but not stereoselectively with simple alkylating agents. Reactions of the anion with selected aldehydes and enones proceeds with some regiocontrol and, with some exceptions, little stereocontrol.
A NEW SULFOXIMINE SYNTHESIS
Harmata, Michael
, p. 437 - 440 (2007/10/02)
Selected sulfonimidoyl halides react with ethylaluminum dichloride to give S-ethyl sulfoximines in good yields.
