195989-07-2

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 195989-06-1 (S)-5-Benzenesulfonyl-1-phenyl-hexan-3-ol 
• 195988-76-2 (R)-4-Benzenesulfonyl-1-chloro-butan-2-ol 
• 195988-82-0 (S)-1-phenyl-5-(phenylsulfonyl)pentan-3-ol 
• 195988-77-3 (R)-3,4-epoxybutyl phenyl sulfone 
• 195988-75-1 4-Chloro-1-phenylsulfonylbutan-3-one 
• 108-98-5 thiophenol 
• 100-39-0 benzyl bromide 
• 61955-91-7 1-chloro-4-(phenylthio)butan-2-one 

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.