131973-93-8

Upstream product

• 123-38-6 propionaldehyde 
• 99930-86-6 (E)-(R)-1-hexenyl p-tolyl sulfoxide 

Downstream Products

• 182879-13-6 (+)-(1'R,2R,3R,S_S)-3-n-butyl-2-(1'-hydroxypropyl)-2-(p-tolylsulfinyl)oxirane 
• 1380096-56-9 (-)-(3S,4E,S(S))-4-(p-tolylsulfinyl)non-4-en-3-yl 2,2,2-trichloroacetimidate 
• 1380096-82-1 (-)-2,2,2-trichloro-N-((5S,3Z,S(S))-4-(p-tolylsulfinyl)non-3-en-5-yl)acetamide 
• 131974-05-5 (E)-5(S)-methyl-4(R_S)-(p-tolylsulfinyl)non-3-ene 
• 131974-06-6 (Z)-5(R)-methyl-4(R_S)-(p-tolylsulfinyl)non-3-ene 
• 479623-90-0 (+)-(E)-4-(p-tolylsulfonyl)non-4-en-3-(S)-ol 
• 1380096-55-8 (+)-(3R,4E,S(S))-4-(p-tolylsulfinyl)non-4-en-3-yl 2,2,2-trichloroacetimidate 
• 1380096-91-2 2,2,2-trichloro-N-((5S,3E,S(S))-4-(p-tolylsulfinyl)non-3-en-5-yl)acetamide 
• 1380096-81-0 (-)-2,2,2-trichloro-N-((5R,3Z,S(S))-4-(p-tolylsulfinyl)non-3-en-5-yl)acetamide 
• 131974-04-4 (Z)-5(S)-methyl-4(R_S)-(p-tolylsulfinyl)non-3-ene 
• 131974-03-3 (E)-5(R)-methyl-4(R_S)-(p-tolylsulfinyl)non-3-ene 
• 182879-05-6 (E)-(R)-4-(Toluene-4-sulfonyl)-non-4-en-3-ol 

Relevant academic research and scientific papers

Nucleophilic epoxidation of α′-hydroxy vinyl sulfoxides

The nucleophilic epoxidation of a variety of α′-(1-hydroxyalkyl) vinyl sulfones and sulfoxides has been studied. The sulfones give rise to anti oxiranes with modest (E) or excellent (Z) selectivities and in good yields. The (E)-sulfoxides display low reactivity within a reinforcing/nonreinforcing scenario. The use of t-BuOOLi in Et2O allows for a highly syn-selective epoxidation-oxidation. The (Z)-sulfoxides display a remarkably high reactivity under these conditions. The reinforcing (S,Ss) diastereomers (3e-g) yield hydroxy sulfinyl oxiranes with high yields and selectivities. In contrast, the (R,Ss) diastereomers (4e-g) show diminished reactivities and a very substrate-dependent stereochemical outcome. The structure of these oxiranes has been secured by chemical correlations and an X-ray crystal structure.

Enantioselective Carbon-Carbon Bond Formation via SN2 Displacements of Acyclic Allylic Mesylates

The copper-mediated SN2′ displacement of enantiomerically pure allylic mesyloxy vinyl sulfoxides takes place with high yields and stereoselectivities. In these adducts, the newly created chiral center is adjacent to a vinyl sulfoxide functionality which should allow for subsequent chirality transfer operations. Alternatively, enantiopure alkenyl sulfones and alkenes bearing an allylic stereocenter are readily available from these adducts with high geometric control. The SN2′ displacements of structurally related mesyloxy sulfides and sulfones with organocuprates have been examined. From a single enantiomer at the allylic alcohol position, the absolute configuration of the new chiral center may be controlled by adjusting the oxidation level on sulfur.

Asymmetric Carbon-Carbon Bond Formation via Sulfoxid-Directed SN2' Displacements of Acyclic Allylic Mesylates

The addition of organocyanocuprates to acyclic allylic mesylates bearing a chiral sulfoxide in the 2-position occurs with complete SN2' regioselectivity, high E/Z stereoselectivity (15:1) and high asymmetric induction to produce enantiomericall