83859-24-9

Upstream product

• 108-94-1 cyclohexanone 
• 1517-82-4 (-)-menthyl p-toluenesulfinate 
• 91796-57-5 4-Methyl-benzenesulfinic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester 
• 83859-16-9 N,N-Dimethyl-N'-[2-((R)-toluene-4-sulfinyl)-cyclohex-(E)-ylidene]-hydrazine 
• 10424-93-8 N'-cyclohexylidene-N,N-dimethyl-hydrazine 
• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 

Downstream Products

• 116049-68-4 (R₁R₂R_S)-2-p-tolylsulfinylcyclohexanol 
• 116049-66-2 (S₁R₂R_S)-2-p-tolylsulfinylcyclohexanol 

Relevant academic research and scientific papers

Synthesis of Chiral Cyclic α-p-Tolylsulphinyl Ketones

Two new syntheses of optically pure cyclic β-oxo sulphoxides are described.Reactions of (-)-menthyl toluene-p-sulphinate with cycloalkanones (CH2)nCO (n = 4, 5, and 6) and iPr2NMgBr yield mixtures of diastereoisomeric sulphoxides without epimerization at sulphur.With the cyclopentanone (n = 4) yields are poor owing to competitive autocondensation of the ketone.Reactions of cycloalkanone N-phenylimines with the sulphinate in the presence of lithium di-isopropylamide afford, after chromatographic purification, the same mixtures of diastereoisomeric β-oxo sulphoxides with no aldolic condensation product.

SYNTHESIS AND REDUCTION OF CHIRAL SULFINYL CYCLOHEXANONES

The reaction of cyclohexanone with (S)-(-)-menthyl-p-toluenesulfinate in the presence of i-Pr2NMgBr yields a mixture of enantiomerically pure 2-p-tolylsulfinylcyclohexanone diastereoisomers.Their stereoselective reduction to chiral hydroxysulfoxides is also reported.