445282-52-0

Upstream product

• 100-52-7 benzaldehyde 
• 479623-81-9 (E)-1-(4-methylphenyl)sulfanyl-1-tributylstannyl-1-hexene 
• 69393-87-9 1-(hex-1-ynylsulfanyl)-4-methylbenzene 

Downstream Products

• 479623-93-3 (+/-)-(Z)-1-phenyl-2-(p-tolylsulfonyl)hept-2-en-1-ol 

Relevant academic research and scientific papers

Asymmetric claisen rearrangements on chiral vinyl sulfoxides

Highly diastereoselective Claisen rearrangements of acyclic allyl vinyl ethers bearing a chiral sulfoxide at C-5 provide γ-δ-unsaturated aldehydes or ketones with up to two consecutive asymmetric centers in the molecule whilst preserving a useful vinyl su

A novel stereoselective synthesis of (2Z)-2-arylsulfanylallylic alcohols by tin-lithium exchange of (E)-αstannylvinyl sulfides

Tin-lithium exchange reaction of (E)-α-stannylvinyl sulfides 1 with n-butyllithium gave (Z)-α-arylsulfanylvinyllithiums 1, which reacted with aldehydes or ketones 3 to afford stereoselectively (2Z)-2-arylsulfanylallylic alcohols 4 in good to high yields.

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.