199934-39-9

Upstream product

• 142176-67-8 (S)-3-Hydroxy-4-((R)-toluene-4-sulfinyl)-butyric acid methyl ester 
• 112572-16-4 lithium (R_S)-(+)-methyl p-tolyl sulfoxide 
• 199934-36-6 (S)-4-Hydroxy-1,5-bis-((R)-toluene-4-sulfinyl)-pentan-2-one 

Relevant academic research and scientific papers

Synthesis of enantiomerically pure 1,3-diols by stereoselective reduction of β-ketosulfoxides. Influence of a stereogenic hydroxylic centre at the δ-position

The influence of the stereogenic hydroxylic carbon at the δ-position of the carbonyl group in 1,5-bis(p-tolylsulfinyl)-4-hydroxy-2-pentanone 1 and 2,6-bis(p-tolylsulfinyl)-5-hydroxy-3-hexanones 2 on the stereochemical course of DIBALH and DIBALH/ZnBr2 reductions has been studied. In contrast with the DIBALH reductions of β-hydroxyketones, that are monitored by the hydroxylic stereogenic carbon, the presence of the sulfinyl group determines a complete 1,3-induction of the sulfur centre.