121703-15-9

Upstream product

• 75-44-5 phosgene 
• 96303-88-7 (-)-10-dicyclohexylsulfamoyl-D-isoborneol 

Downstream Products

• 121666-45-3 (R)-{(1S,2R,4R)-1-[(Dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yloxycarbonylamino}-(4-methoxy-phenyl)-acetic acid methyl ester 
• 125416-28-6 E-10-dicyclohexylsulfamoyl-D-isobornyl 4-hydroxypent-2-enoate 
• 125416-29-7 E-10-dicyclohexylsulfamoyl-D-isobornyl 4-hydroxyhex-2-enoate 
• 125416-30-0 E-10-dicyclohexylsulfamoyl-D-isobornyl 4-hydroxyhept-2-enoate 
• 125416-33-3 E-10-dicyclohexylsulfamoyl-D-isobornyl 4-hydroxy-5-cyclohexylpent-2-enoate 
• 125416-32-2 E-10-dicyclohexylsulfamoyl-D-isobornyl 4-hydroxy-5-methylhex-2-enoate 
• 125416-31-1 E-10-dicyclohexylsulfamoyl-D-isobornyl 4-hydroxy-5-phthalimidopent-2-enoate 
• 125473-42-9 (E)-(S)-6-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-hydroxy-hex-2-enoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 125416-34-4 (E)-(R)-6-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-hydroxy-hex-2-enoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 125473-38-3 (E)-(S)-4-Hydroxy-hept-2-enoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 125416-30-0 (E)-(R)-4-Hydroxy-hept-2-enoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 125473-37-2 (E)-(S)-4-Hydroxy-hex-2-enoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 125416-29-7 (E)-(R)-4-Hydroxy-hex-2-enoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 125416-28-6 (E)-(R)-4-Hydroxy-pent-2-enoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 

Relevant academic research and scientific papers

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).

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.

ACYCLIC STEREOSELECTION IN α-AMIDOALKYLATION REACTIONS

The chiral reagent 7 provides the first example of an acyclic α-amidoalkylation reagent that generates a new stereogenic center with excellent stereoselectivity, and the stereochemistry of the resulting products provides evidence that the N-acylimine inte