208447-87-4

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 
• 182184-47-0 [4S,5S,(S)R]-4-hydroxy-5-methyl-4-[(p-tolylsulfinyl)methyl]-2-cyclohexenone 
• 851129-82-3 (4R,5R)-6-Bromo-4-hydroxy-5-methyl-4-((R)-toluene-4-sulfinylmethyl)-cyclohex-2-enone 
• 208447-85-2 (4R,5R,6S)-6-Bromo-4-hydroxy-5-methyl-4-((R)-toluene-4-sulfinylmethyl)-cyclohex-2-enone 

Downstream Products

• 851129-84-5 (4R)-4-hydroxy-3-methyl-4-[(p-tolylsulfonyl)methyl]-2,5-cyclohexadien-1-one 

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

Studies of Diastereoselectivity in Conjugate Addition of Organoaluminum Reagents to (R)-[(p-Tolylsulfinyl)methyl]quinols and Derivatives

(R)-4-Hydroxy-4-[p-tolylsulfinyl)methyl]-2,5-cyclohexadienones 1-3, and 6 reacted with organoaluminum derivatives from the pro-R conjugated position in a highly π-facial diastereoselective manner directed by the C-4 OH. A similar facial diastereoselectivity arose from reactions with 3-alkylsubstituted analogues 4 and 5 and 5-alkyl-4-hydroxy-4-[(p-tolylsuIfinyl)methyl]-2-cyclohexenones 10a,b. Semiempirical calculations (AM1 model) provide data on transition-state energies for additions in full agreement with the experimental results.