97827-42-4

Upstream product

• 125416-24-2 (1R,2S,5R)-menthyl 4-chlorophenylsulfinylacetate 
• 123-38-6 propionaldehyde 
• 125382-46-9 (1R,2S,5R)(-)-menthyl-4-chlorophenylsulfenylacetate 
• 2216-51-5 (-)-menthol 
• 57564-56-4 (E)-Pent-2-enoic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 16832-20-5 (1R,2S,5R)-menthol bromoacetate 

Relevant academic research and scientific papers

Stereochemically matched sulfinylacetates for double diastereoselection in the spac reaction

4-Chlorophenylsulfinylacetates of defined stereochemistry at sulfur were prepared from monochiral alcohols: compound 2 from (+)-menthol; 3 and 4 from (-)-8-phenylmenthol; 5 and 6 from (+)-trans-2-phenylcyclohexanol; and, 7 and 9 from (-)-10-dicyclohexylsulfamoyl-D-isoborneol. Reagents for which the sulfoxide asymmetry is matched with the inducing effect of the auxiliary give good diastereoselection in SPAC reactions affording γ-hydroxy-α,β-unsaturatod alcohols of high optical purity. Asymmetry at the sulfoxide has a greater effect than the auxiliaries on the stereochemical outcome of these reactions.