518316-68-2

Upstream product

• 1519-39-7 (R)-methyl p-tolyl sulfoxide 
• 170117-33-6 [(S)R]-4-hydroxy-4-[p-(tolylsulfinyl)methyl]cyclohexa-2,5-dienone 

Downstream Products

• 518316-72-8 (1S,4R,6S)-6-methyl-1-[(p-tolylsulfonyl)methyl]cyclohex-2-ene-1,4-diol 
• 518316-73-9 (1S,4R,6S)-4-[(tert-butyldimethylsilyl)oxy]-6-methyl-1-[(p-tolylsulfonyl)methyl]cyclohex-2-en-1-ol 
• 518316-74-0 (4R,6S)-4-[(tert-butyldimethylsilyl)oxy]-6-methyl-2-cyclohexenone 
• 931103-80-9 (4R,6S)-4-hydroxy-6-methylcyclohex-2-enone 

Relevant academic research and scientific papers

Enantioselective synthesis of natural polyoxygenated cyclohexanes and cyclohexenes from [(p-tolylsulfinyl)methyl]-p-quinols

Exploitation of the β-hydroxysulfoxide fragment present in a number of enantiomerically pure (SR)and (SS)-[(p-tolylsulfinyl)methyl]-pquinols allowed chemo- and stereocontrolled conjugate additions of different organoaluminium reagents to the cyclohexadien

Enantioselective synthesis of (+)- and (-)-dihydroepiepoformin and (+)-epiepoformin

(Chemical Equation Presented) The enantioselective synthesis of both enantiomers of dihydroepiepoformin (1) and (+)-epiepoformin (2) was achieved from (p-tolylsulfinyl)-methyl-p-quinols (SR)- or (SS)-3 and (4R,SR)-4, respectively. Key features include the

β-hydroxysulfoxides as chiral cyclic ketone equivalents: Enantioselective synthesis of polysubstituted cyclohexanones, cyclohexenones and cyclohexenediones

The β-hydroxysulfoxide moiety, after oxidation to sulfone, acts as a masked carbonyl group in a cyclic system, opening an easy access to differently substituted enantiomerically pure cyclic ketones by means of aluminium-mediated conjugate additions, stereoselective reductions and elimination by retrocondensation in basic medium.