4850-72-0

Upstream product

• 3019-19-0 tert-butyl phenyl sulfide 
• 591-51-5 phenyllithium 
• 66967-37-1 2-Methyl-propane-2-sulfinic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 126494-96-0 2,2-diphenyl-1,2-dihydroxypropyl 2-O-tert-butylsulfinate 
• 591-50-4 iodobenzene 
• 60011-16-7 (_SS)-(+)-tert-butyl tert-butanethiosulfinate 
• 100-59-4 phenylmagnesium chloride 
• 62076-10-2 (tert-butylsulfinyl)benzene 
• 108-86-1 bromobenzene 
• 126494-96-0 2-Methyl-propane-2-sulfinic acid (S)-2-hydroxy-1-methyl-2,2-diphenyl-ethyl ester 
• 100-58-3 phenylmagnesium bromide 
• 939962-74-0 bis(2,2’-bromophenyl) sulfoxide 
• 1150662-18-2 (2-bromophenyl) isopropyl sulfoxide 
• 4170-69-8 isopropyl phenyl sulfoxide 

Downstream Products

• 885130-27-8 [1R,(S)S]-(-)-N-{[2-(tert-butylsulfinyl)phenyl]phenylmethyl}-4-methylbenzenesulfonamide 
• 885130-25-6 [1S,(S)S]-(-)-N-{[2-(tert-butylsulfinyl)phenyl]phenylmethyl}-4-methylbenzenesulfonamide 
• 885130-43-8 (S)-(+)-2,3-dihydro-3-isopropyl-2-(toluene-4-sulfonyl)benzo[d]isothiazole 
• 627503-87-1 N-[(S)-2-methyl-1-phenylpropan-1-yl]-4-methylbenzenesulfonamide 
• 1092722-67-2 (-)-(S)-tert-butyl [(2-diphenylphosphanyl)phenyl] sulfoxide 
• 1242149-01-4 (S)-bis[2-(tert-butylsulfinyl)phenyl] diselenide 
• 1161947-12-1 [1R,S(R)]-N-[(2-tert-butylsulfinylphenyl)phenylmethyl]-4-methylbenzenesulfonamide 
• 1161947-19-8 (R)-2,3-dihydro-3-phenyl-2-(tert-butoxycarbonyl)benzo[d]isothiazole 
• 1161947-16-5 C₂₂H₂₉NO₃S 
• 1161947-11-0 [1R,S(R)]-N-[1-cyclohexyl-1-(2-tert-butylsulfinylphenyl)-methyl]-4-methylbenzenesulfonamide 
• 1161947-13-2 [1R,S(R)]-N-[1-(m-bromophenyl)-1-(2-tert-butylsulfinylphenyl)-methyl]-4-methylbenzenesulfonamide 
• 1064197-27-8 [1R,S(R)]-N-[2-methyl-1-(2-tert-butylsulfinylphenyl)-propyl]-4-methylbenzenesulfonamide 
• 1161947-14-3 C₂₂H₃₉NO₃S₂Si 
• 1161947-15-4 tert-butyl [1R,S(R)]-1-[2-(tert-butylsulfinyl)phenyl]-2-methylpropylcarbamate 

Relevant academic research and scientific papers

Chiral Br?nsted-Acid-Catalyzed Asymmetric Oxidation of Sulfenamide by Using H2O2: A Versatile Access to Sulfinamide and Sulfoxide with High Enantioselectivity

Herein, we describe an example of catalytic asymmetric synthesis of sulfinamides. Aromatic sulfenamides were chosen as useful substrates, because of the indispensable N-H bond, which could form an efficient hydrogen bond with chiral phosphoric acid. Hsub

Stereoselective synthesis of isoindolinones and tert-butyl sulfoxides

A reaction of Grignard reagents with an optically pure N-sulfinylimine derived from methyl 2-formylbenzoate yields enantioenriched isoindolinones and tert-butyl sulfoxides. The products are formed by the addition of the nucleophile to N-sulfinylimine followed by cyclization to form N-tert-butylsulfinylisoindolinone, which readily undergoes substitution with a second equivalent of Grignard reagent. The reaction can be carried out in dichloromethane at room temperature or at elevated temperatures without any loss of stereoselectivity. The use of nucleophiles other than Grignard reagents has also been investigated.

Multivariate Metal-Organic Frameworks as Multifunctional Heterogeneous Asymmetric Catalysts for Sequential Reactions

The search for versatile heterogeneous catalysts with multiple active sites for broad asymmetric transformations has long been of great interest, but it remains a formidable synthetic challenge. Here we demonstrate that multivariate metal-organic frameworks (MTV-MOFs) can be used as an excellent platform to engineer heterogeneous catalysts featuring multiple and cooperative active sites. An isostructural series of 2-fold interpenetrated MTV-MOFs that contain up to three different chiral metallosalen catalysts was constructed and used as efficient and recyclable heterogeneous catalysts for a variety of asymmetric sequential alkene epoxidation/epoxide ring-opening reactions. Interpenetration of the frameworks brings metallosalen units adjacent to each other, allowing cooperative activation, which results in improved efficiency and enantioselectivity over the sum of the individual parts. The fact that manipulation of molecular catalysts in MTV-MOFs can control the activities and selectivities would facilitate the design of novel multifunctional materials for enantioselective processes.

Atropo-diastereoselective coupling of aryllithiums and arynes — variations around the chiral auxiliary

The atropo-selective coupling of in situ generated arynes and aryllithiums bearing various chiral auxiliaries ortho to lithium (tert-butylsulfoxide, para-tolylsulfoxide, tartrate-derived chiral diethers and oxazolines) is described. Chiral oxazolines showed the best results in terms of yields of coupling products. Different reaction parameters like the nature of the aryne precursor, the oxazoline, the alkyllithium base or the solvent revealed to be crucial for obtaining good yields and for diastereoselection.

Diastereoconvergent synthesis of trans -5-hydroxy-6-substituted-2- piperidinones by addition-cyclization-deprotection process

A diastereoselective one-pot approach to access trans-5-hydroxy-6- substituted-2-piperidinones by an addition-cyclization-deprotection process has been developed, in which the stereogenic center at the C-6 position was solely controlled by α-OTBS group. The utility of this transformation is demonstrated by the asymmetric synthesis of the enantiomer of (-)-CP-99,994.

PROCESS FOR THE ASYMMETRIC OXIDATION OF ORGANIC COMPOUNDS WITH PEROXIDES IN THE PRESENCE OF A CHIRAL ACID CATALYST

The present invention relates to a process for the asymmetric oxidation of nucleophilic organic compounds, particularly metal-free, with peroxide compounds in the presence of a chiral Bronsted acid catalyst. In one detail, the present invention relates to a process for enantioselective sulfoxidation of thiocompounds with peroxide compounds in the presence of a chiral imidodiphosphate catalyst. In another detail, the present invention relates to a process for enantioselective sulfoxidation of thiocompounds with peroxide compounds in the presence of a chiral phosphoric acid catalyst.

Enantioselective access to benzannulated spiroketals using a chiral sulfoxide auxiliary

This article describes our efforts to develop an asymmetric synthesis of bisbenzannulated spiroketals using a chiral sulfoxide auxiliary. Our primary focus was on the synthesis of the 3H-spiro[benzofuran-2,2′-chroman] ring system, the spirocyclic core of the rubromycin family. Our strategy employed the use of lithium-halogen exchange on a racemic bromospiroketal in order to attach a chiral sulfoxide, thus producing two diastereomers. The diastereomers were separable, enabling isolation of each spiroketal enantiomer. Subsequent cleavage of the sulfoxide group from each diastereomer yielded the respective parent spiroketal in high enantiopurity.

BINOL derived C2-symmetric bis-sulfinates as efficient sulfinyl transfer agents in the synthesis of tert-butyl sulfoxides

The reaction of novel C2-symmetric bis-sulfinate esters derived from (R)-BINOL with Grignard reagents affords tert-butyl sulfoxides in ee up to 97%. The desired enantiomer can be generated at will by the proper selection of BINOL.

Desymmetrization of prochiral diaryl sulfoxides by an asymmetric sulfoxide-magnesium exchange

The first desymmetrizations of prochiral diaryl sulfoxides 1 by an asymmetric sulfoxide-magnesium exchange reaction are reported. The respective substrate (1), iPr2Mg, and the dilithium salt of (S)-BINOL (which was prepared in situ) provided (S)-configured aryl isopropyl sulfoxides 2 in up to 91 % yield and with up to 91 % ee. (S)-BINOL was re-isolable in 98 % yield. Copyright

Tert-Butanesulfinylthioether ligands: Synthesis and application in palladium-catalyzed asymmetric allylic alkylation

A class of novel chiral SO-S-type bidentate ligands based on the tert-butylsulfinyl moiety as the sole chiral source were designed and synthesized through a simple and efficient pathway. These ligands are effective catalyst precursors for the palladium-catalyzed allylic alkylation of 1,3-diphenyl-2-propenyl acetate and moderate to good stereoselectivities (up to 84% ee) were obtained.