50299-85-9

Upstream product

• 14633-55-7 cyclopropyl 4-methylphenyl sulfide 
• 4333-56-6 cyclopropyl bromide 
• 1517-82-4 (-)-menthyl p-toluenesulfinate 

Downstream Products

• 106358-73-0 (Ss)-1-(1-Hydroxy-1-phenylethyl)-1-p-toluenesulfinylcyclopropane 
• 106358-72-9 (Ss)-1-(1-Hydroxy-1-phenylethyl)-1-p-toluenesulfinylcyclopropane 
• 128175-66-6 Toluene-4-sulfonic acid (S)-1-phenyl-1-[1-((S)-toluene-4-sulfinyl)-cyclopropyl]-ethyl ester 
• 128175-65-5 Toluene-4-sulfonic acid (R)-1-phenyl-1-[1-((S)-toluene-4-sulfinyl)-cyclopropyl]-ethyl ester 
• 128175-64-4 Methanesulfonic acid (S)-1-phenyl-1-[1-((S)-toluene-4-sulfinyl)-cyclopropyl]-ethyl ester 
• 128175-63-3 Methanesulfonic acid (R)-1-phenyl-1-[1-((S)-toluene-4-sulfinyl)-cyclopropyl]-ethyl ester 
• 128175-68-8 1-Methyl-4-((S)-(S)-4-methyl-4-phenyl-cyclobut-1-enesulfinyl)-benzene 
• 106375-24-0 1-Methyl-4-((S)-(R)-4-methyl-4-phenyl-cyclobut-1-enesulfinyl)-benzene 
• 128175-67-7 (S)-(+)-4-Methyl-4-phenyl-1-p-toluenesulfenylcyclobutene 
• 128175-61-1 (S)-1-Benzoyl-1-p-toluenesulfinylcyclopropane 
• 128175-62-2 (S)-1-Acetyl-1-p-toluenesulfinylcyclopropane 
• 106358-76-3 1-((S)-(S)-4-Ethyl-4-methyl-cyclobut-1-enesulfinyl)-4-methyl-benzene 
• 106358-78-5 1-((S)-4-Ethyl-4-methyl-cyclobut-1-enylsulfanyl)-4-methyl-benzene 
• 106358-77-4 (R)-(-)-4-Methyl-4-phenyl-1-p-toluenesulfenylcyclobutene 

Relevant academic research and scientific papers

Chemistry of oxaziridines. 17. N-(phenylsulfonyl)(3,3-dichlorocamphoryl)oxaziridine: A highly efficient reagent for the asymmetric oxidation of sulfides to sulfoxides

The synthesis, structure, and enantioselective oxidations of a new chiral N-sulfonyloxaziridine 12c [3,3-dichloro-1,7,7-trimethyl-2'-(phenylsulfonyl)spiro[bicyclo[2.2.1]heptane-2, 3'-oxaziridine]] are reported. This oxidant, which exhibits remarkably high and predictable ee's for the enantioselective oxidation of prochiral sulfides to sulfoxides, is prepared in three steps from (+)- or (-)-camphor in 50% overall yield. Steric effects are primarily responsible for the molecular recognition and are predictable using a simple active-site model where the nonbonded interactions between the RL and RS groups of the sulfide (RL-S-RS) and the active-site surface are minimized in a planar transition-state structure. The fact that alkyl aryl sulfides give high ee's in nonpolar solvents suggests that there is also a stereoelectronic component to the molecular recognition. High ee's (>90%) are anticipated for those sulfides where the difference in size of the groups directly bonded to the sulfur atom is large, i.e., aryl, tert-butyl vs CH2R (R = H, alkyl, benzyl, etc). The X-ray structure and studies with the dihydro, difluoro, and dibromo oxaziridines 12a, 12b, and 12d reveal that the exceptional enantioselectivities displayed by 12c are a consequence of a molecular cleft or groove, defined by the oxaziridine chlorine atoms and phenylsulfonyl group, on the active-site surface.