308818-87-3

Upstream product

• 50444-99-0 (1R,2S,5R)-menthyl-(S)-p-toluenesulfinate 
• 1519-40-0 (+)-(R)-ethyl p-tolyl sulfoxide 
• 100-52-7 benzaldehyde 

Downstream Products

• 107647-76-7 (S_S,1S)-1-phenyl-2-(p-tolylsulfinyl)-2-propen-1-ol 
• 107647-79-0 (S_S,1R)-1-phenyl-2-(p-tolylsulfinyl)-2-propen-1-ol 
• 308818-93-1 (3S,S_S)-3-benzoyloxy-3-phenyl-2-(p-tolylsulfinyl)-1-propene 
• 308818-91-9 (S_S)-1-hydroxy-1-phenyl-2-(phenylselenyl)-2-(p-tolylsulfinyl)propane 

Relevant academic research and scientific papers

Diastereoselective Radical Hydrogenation of α-(1-Hydroxyalkyl)vinyl Sulfoxides and Sulfones Controlled by Intramolecular Hydrogen Bonding

The reaction of (S)-α-(1-hydroxyalkyl)vinyl sulfoxides (S)-5 with alkyl radicals and tributyltin hydride gave the addition-hydrogenation products with high diastereoselectivity, whereas the reaction with (R)-α-(1-hydroxyalkyl)vinyl sulfoxides (R)-5 resulted in complete recovery of the starting sulfoxides. Stereoselective intramolecular hydrogen bonding between the hydroxy group and the diastereotopic sulfonyl oxygen led to high diastereoselectivity in the radical reaction of α-(1-hydroxyethyl)vinyl sulfone 12. An important role of intramolecular hydrogen bonding on the diastereoselectivity as well as the reactivity toward alkyl radicals is discussed.