107978-06-3

Upstream product

• 107978-05-2 Naphthalene-1-thiosulfonic acid S-phenyl ester 
• 93-55-0 1-phenyl-propan-1-one 
• 931-59-9 benzenesulfenyl chloride 
• 52322-54-0 2-(phenylthio)benzo[d]isothiazol-3(2H)-one 1,1-dioxide 
• 66323-99-7 trimethyl[(Z)-(1-phenyl-1-propenyl)oxy]silane 
• 69358-34-5 1-phenyl-2-phenylsulfanyl-2-propen-1-ol 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 108-98-5 thiophenol 
• 37471-46-8 1-phenyl-1-trimethylsiloxypropene 

Downstream Products

• 56819-81-9 1-phenyl-2-phenylsulfanylpropan-1-ol 
• 4541-87-1 cis-1-phenylpropene oxide 

Relevant academic research and scientific papers

High-Atom Economic Approach to Prepare Chiral α-Sulfenylated Ketones

Chiral α-sulfenylated ketones are versatile building blocks, although there are still several limitations with their preparation. Here we report a new two-step procedure, consisting of Pd-catalyzed hydrothiolation of propargylic alcohols followed by an enantioselective Rh isomerization of allylic alcohols. The isomerization reaction is the key step for obtaining the ketones in their enantioenriched form. The new methodology has a high atom economy and induces good to high levels of enantioselectivity; no waste is produced. A mechanism involving a Rh-hydride-enone intermediate is proposed for the isomerization reaction.

Catalytic, Enantioselective Sulfenylation of Ketone-Derived Enoxysilanes

A catalytic, enantioselective, Lewis base-catalyzed α-sulfenylation of silyl enol ethers has been developed. To avoid acidic hydrolysis of the silyl enol ether substrates, a sulfenylating agent that did not require additional Br?nsted acid activation, namely N-phenylthiosaccharin, was developed. Three classes of Lewis bases - tertiary amines, sulfides, and selenophosphoramides - were identified as active catalysts for the α-sulfenylation reaction. Among a wide variety of chiral Lewis bases in all three classes, only chiral selenophosphoramides afforded α-phenylthio ketones in generally high yield and with good enantioselectivity. The selectivity of the reaction does not depend on the size of the silyl group but is highly sensitive to the double bond geometry and the bulk of the substituents on the double bond. The most selective substrates are those containing a geminal bulky substituent on the enoxysilane. Computational analysis revealed that the enantioselectivity arises from an intriguing interplay among sterically guided approach, distortion energy, and orbital interactions.

Asymmetric Sulfenylation of Tin(II) Enolates of Ketones and 3-Acyl-2-oxazolidones. Application to the Synthesis of Optically Active Epoxides

In the presence of chiral diamines, the reaction between tin(II) enolates of ketones or 3-acyl-2-oxazolidones and thiosulfonates proceeds smoothly to give the corresponding β-keto sulfides with high enetioselectivity.Further, optically active epoxides are prepared from these β-keto sulfides.