20675-59-6

Upstream product

• 66-77-3 1-naphthaldehyde 
• 108771-12-6 4-((S)-Toluene-4-sulfinyl)-pyridine 
• 108771-11-5 (S_S)-3-(p-tolylsulfinyl)pyridine 
• 144539-55-9 (+)-(S)-1-bromovinyl-p-tolyl sulfoxide 
• 3699-01-2 4-tolyl phenyl sulfide 
• 190448-86-3 4-Methyl-benzenesulfinic acid (S)-pent-(E)-ylideneamide 
• 220732-34-3 (S)-(E)-N-ethylidene-4-methylbenzenesulfinamide 
• 21179-27-1 (S)-(+)-N,N,4-trimethylbenzenesulfinamide 
• 59336-80-0 1,2-Dibrom-1-p-tolylsulfinylethan 
• 591-51-5 phenyllithium 
• 165904-22-3 4,4,5,5-tetramethyl-2-phenethyl-1,3,2-dioxaborolane 
• 676593-26-3 5,5-dimethyl-2-(2-phenylethyl)benzo-1,3,2-dioxaborinate 
• 108-98-5 thiophenol 
• 624-31-7 4-tolyl iodide 

Relevant academic research and scientific papers

New general sulfinylating process for asymmetric synthesis of enantiopure sulfinates and sulfoxides

(Chemical Equation Presented) A general process for the efficient synthesis of sulfinyl transfer agents has been developed using cinchona alkaloids quinine and quinidine as chiral auxiliaries. The importance of these new and unique sulfinyl transfer agent

Programmed synthesis of a contiguous stereotriad motif by triple stereospecific reagent-controlled homologation

All distinct diastereoisomers of a contiguous stereotriad motif were separately targeted by a triple chain extension of B-phenethyl boronic esters using four unique presentation sequences of enantiomorphs of 1-[ 2H]-1-chloro-2-(1,3-dioxolan-2-yl)ethyllithium. The (R)- or (S)-configured chloroalkyllithium reagents were generated by sulfoxide-lithium exchange from the appropriate scalemic p-tolyl chloroalkyl sulfoxides using phenyllithium (THF, -78 C). Stereotriad synthesis was accomplished in a single reaction vessel [7-19% yield, typical dr ≥ 74 (target):26 (Σ all other isomers)] and implemented by a simple algorithm consisting of reagent charging and temperature cycling events.

Syntheses and Reactions of Optically Active Alkoxyaminosulfonium Salts

The optically active methoxymorpholino-p-tolylsulfonium salt has been synthesized by the reaction of optically active N-p-toluenesulfinylmorpholine with methyl trifluoromethanesulfonate.The sulfonium ion methylated benzylethylphenylamine and benzyl ethyl sulfide with assymetric induction to give the optically active benzylethylmethylphenylammonium ion and benzylethylmethylsulfonium ion respectively.The optically active methoxymorpholino-p-tolylsulfonium salt and diaminosulfonium salts have been prepared in a one pot reaction between N-p-toluenesulfenylmorpholine and 1-chlorobenzotriazole with methanol in the presence of 1-menthol at -80 deg C.

Palladium/PC-Phos-Catalyzed Enantioselective Arylation of General Sulfenate Anions: Scope and Synthetic Applications

Herein we reported an efficient palladium-catalyzed enantioselective arylation of both alkyl and aryl sulfenate anions to deliver various chiral sulfoxides in good yields (up to 98%) with excellent enantioselectivities (up to 99% ee) by the use of our developed chiral O,P-ligands (PC-Phos). PC-Phos are easily prepared in short steps from inexpensive commercially available starting materials. The single-crystal structure of the PC4/PdCl2 showed that a rarely observed 11-membered ring was formed via the O,P-coordination with the palladium(II) center. The salient features of this method include general substrate scope, ease of scale-up, applicable to the late-stage modification of bioactive compounds, and the synthesis of a marketed medicine Sulindac.

Investigation of steric and electronic effects in the copper-catalysed asymmetric oxidation of sulfides

Steric and electronic effects in the copper-catalysed asymmetric oxidation of aryl benzyl, aryl alkyl and alkyl benzyl sulfides have been investigated. The presence of an aryl group directly attached to the sulfur is essential to afford sulfoxides with high enantioselectivities, with up to 97% ee for 2-naphthyl benzyl sulfoxide, the highest enantioselectivity achieved to date for copper-catalysed asymmetric sulfoxidation. In contrast, the benzyl substituent can be replaced by sterically comparable groups with no effect on enantioselectivity. Copper-mediated oxidation of substituted aryl benzyl sulfides display modest steric and electronic effects resulting in comparable or lower enantioselectivities to those obtained with the unsubstituted benzyl phenyl sulfide.

Stereochemical studies of the palladium-catalyzed rearrangements of chiral 2-alkynyl sulfinates into chiral allenyl sulfones

Palladium-catalyzed reactions of diastereomerically pure chiral 2-alkynyl p-toluenesulfinates under very mild reaction conditions gave both enantiomers of optically active sulfonyl allenes in good yields with high stereospecificity. The stereochemistry of this transformation with the assistance of a palladium catalyst was determined. The conversion rate was measured by the HPLC analysis in accordance with the elapse of the reaction time, and the rather marked difference of the rate was observed between the diastereomeric sulfinates. A novel mechanism for this transformation with palladium catalysts is proposed.

Stereoselective addition to chiral p-toluene sulfinimines

Diastereoselective addition of a number of Grignard reagents to chiral p-toluene sulfinimines 2b-2d under the mediation of copper salts afforded various protected α-branched amines. (C) 2000 Elsevier Science Ltd.

A novel route to enantiomerically pure sulfoxides through displacement of a carbon leaving group

Enantiomerically pure sulfoxides were produced by reaction of dimethyl (S)-p-tolyl-sulfinylmethylphosphonate with the suitable Grignard reagents. Yields up to 75% were obtained.

Sulfoxides of High Enantiopurity from Bacterial Dioxygenase-catalysed Oxidation

Selected strains of the bacterium Pseudomonas putida (previously shown to effect dioxygenase-catalysed asymmetric cis-dihydroxylation of alkenes) have been found to yield chiral sulfoxides from the corresponding sulfides with a strong preference for the (R)- or (S)-configurations but without evidence of sulfone formation; similar results obtained using an Escherichia coli clone (pKST11, containing the Tod C1 C2 B and A genes encoding toluene dioxygenase from P. putida NCIMB 11767) are again consistent with a stereoselective dioxygenase-catalysed sulfoxidation.

Optically active sulfoxides by enantiospecific reactions of bromovinyl aryl sulfoxides with grignard reagents

Optically active bromovinyl aryl sulfoxides were subjected to reactions with phenyl- or alkyl-magnesium compounds, with the production of optically active diaryl or aryl alkyl sulfoxides, with inversion of configuration. The enantiospecificity of the process was found to be 98-100%.