195988-76-2

Upstream product

• 108-98-5 thiophenol 
• 61955-91-7 1-chloro-4-(phenylthio)butan-2-one 
• 195988-75-1 4-Chloro-1-phenylsulfonylbutan-3-one 

Downstream Products

• 195988-77-3 (R)-3,4-epoxybutyl phenyl sulfone 
• 195988-86-4 Toluene-4-sulfonic acid (S)-1-(2-benzenesulfonyl-ethyl)-dodecyl ester 
• 195988-93-3 Toluene-4-sulfonic acid (R)-1-(2-benzenesulfonyl-ethyl)-dodecyl ester 
• 195988-90-0 Toluene-4-sulfonic acid (S)-3-benzenesulfonyl-1-phenethyl-propyl ester 
• 195988-95-5 Toluene-4-sulfonic acid (R)-3-benzenesulfonyl-1-phenethyl-propyl ester 
• 195988-85-3 Toluene-4-sulfonic acid (S)-1-(2-benzenesulfonyl-ethyl)-hexyl ester 
• 195988-92-2 Toluene-4-sulfonic acid (R)-1-(2-benzenesulfonyl-ethyl)-hexyl ester 
• 195988-87-5 Toluene-4-sulfonic acid (S)-1-(2-benzenesulfonyl-ethyl)-4-methyl-pentyl ester 
• 195988-94-4 Toluene-4-sulfonic acid (R)-1-(2-benzenesulfonyl-ethyl)-4-methyl-pentyl ester 
• 195989-07-2 Toluene-4-sulfonic acid (S)-3-benzenesulfonyl-1-phenethyl-butyl ester 
• 195989-06-1 (S)-5-Benzenesulfonyl-1-phenyl-hexan-3-ol 
• 195988-80-8 (S)-1-Benzenesulfonyl-tetradecan-3-ol 
• 195988-82-0 (S)-1-phenyl-5-(phenylsulfonyl)pentan-3-ol 
• 195988-79-5 (S)-1-Benzenesulfonyl-octan-3-ol 

Relevant academic research and scientific papers

Synthesis of enantiomerically pure (1R,2R)- and (1S,2S)-2-alkyl-1-phenylsulfonylcyclopropanes using Bakers' yeast

Reduction of the ketone 1 with Bakers' yeast gives the alcohol (R)-2 with high enantiomeric excess, and this upon subsequent epoxidation and alkylation with Grignard reagents provides the alcohols (S)-4 without racemisation. Tosylation of the alcohols (S)-4 under common conditions yields the tosylates (toluene-p-sulfonates) (S)-5, whilst under Mitsunobu conditions inversion of configuration takes place giving the tosylates (R)-5. Subsequent treatment of the tosylates (S)-5 and (R)-5 with lithium diisopropylamide leads to cyclization affording the enantiomerically pure cyclopropanes (S,S)-6 and (R,R)-6 in high yields, respectively. The diastereoisomeric alcohol (S)-4f, obtained by methylation of the alcohol (S)-4e, can also be converted into the single stereoisomer (R,R)-6f in enantiomerically pure form.