125416-32-2

Upstream product

• 121703-15-9 10-dicyclohexylsulfamoyl-D-isobornyl chloroformate 
• 125382-47-0 10-dicyclohexylsulfamoyl-D-isobornyl 4-chlorophenylsulfenylacetate 
• 125382-45-8 (2RS)-(1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl bromoacetate 
• 96303-88-7 (-)-10-dicyclohexylsulfamoyl-D-isoborneol 
• 125416-26-4 10-dicyclohexylsulfamoyl-D-isobornyl (R)(+)-4-chlorophenylsulfinylacetate 
• 590-86-3 isovaleraldehyde 

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.

STEREOSELECTIVE SYNTHESES OF γ-HYDROXY-α,β-UNSATURATED ESTERS: AN ASYMMETRIC VERSION OF THE "SPAC" REACTION

Double diastereoselection in the Sulfoxide Piperidine And Carbonyl (SPAC) reactions of sulfinyl acetate esters (2) with α-unsubstituted aldehydes (3) has been investigated to facilitate asymmetric syntheses of γ-hydroxy-α,β-unsaturated esters (1).