33903-50-3

Usage

Uses

Different sources of media describe the Uses of 33903-50-3 differently. You can refer to the following data:
1. A new ligand for assymmetric catalysis
2. A new ligand for assymmetric catalysis.

Synthesis Reference(s)

Journal of the American Chemical Society, 92, p. 6594, 1970 DOI: 10.1021/ja00725a035

InChI:InChI=1/C7H11NOS/c1-10(8,9)7-5-3-2-4-6-7/h2-6,10H,1H3,(H2,8,9)

Upstream product

• 1193-82-4 (S)-methylphenylsulfoxide 
• 4381-25-3 S-methyl-S-phenylsulfoximine 
• 1193-82-4 racemic methyl phenyl sulfoxide 
• 4850-71-9 (R)-methyl phenyl sulfoxide 
• 1039027-81-0 (S)-N-cyclohex-1-enyl-S-methyl-S-phenylsulfoximine 
• 100-68-5 methyl-phenyl-thioether 
• 1466-88-2 2-nitrocinnamic aldehyde 
• 49678-08-2 3-(4-nitrophenyl)-propenal 
• 78024-61-0 2-((E)-3-Oxo-propenyl)-benzoic acid methyl ester 
• 66223-53-8 trans-2-bromocinnamaldehyde 
• 104-55-2 3-phenyl-propenal 
• 2009-97-4 ethyl 2-diazo-3-oxobutanoate 
• 13298-76-5 tert-butyl 2-diazo-3-oxobutanoate 
• 28383-65-5 ethyl 2-diazo-3-oxo-3-phenylpropanoate 

Downstream Products

• 100326-78-1 (+)-(S)-1,5-diphenyl-1H-1λ⁴,2,4-thiadiazine 1-oxide 
• 33993-53-2 N,S-dimethyl-S-phenylsulfoximine 
• 177914-36-2 (+)-(S)-N-benzyl-S-methyl-S-phenylsulfoximine 
• 188633-73-0 (S_S)-N-(N-tert-Butyloxycarbonyl-L-prolinyl)-S-methyl S-phenyl sulfoximine 
• 188633-56-9 (S_S)-N-tert-Butyloxycarbonyl S-methyl-S-phenyl sulfoximine 
• 210552-35-5 (+)-(S)-N-(2-Hydroxyethyl)-S-methyl-3-phenylsulfoximine 
• 210552-36-6 (+)-(S)-N-(3-Hydroxypropyl)-S-methyl-S-phenylsulfoximine 
• 337363-01-6 (S_S)-N-(N-tert-Butyloxycarbonyl-L-alanyl)-S-methyl S-phenyl sulfoximine 
• 337363-02-7 (S_S)-N-(N-tert-Butyloxycarbonyl-L-tert-leucinyl)-S-methyl S-phenyl sulfoximine 
• 623575-50-8 C₂₁H₂₆N₂O₄S 

Relevant academic research and scientific papers

An efficient resolution of (±)-S-methyl-S-phenylsulfoximine with (±)-10-camphorsulfonic acid by the method of half-quantities

Racemic S-methyl-S-phenylsulfoximine (±)-1 can be resolved with only 0.6 equivalents of (+)-camphorsulfonic acid by avoiding any recrystallization to give (+)-1 of ≤99% ee in 80% yield and (-)-1 of 97-99% ee in 74% yield. This procedure, which is based on

The search for benchrotrenes and ferrocenes containing a chiral sulfoximido group: Preparation and structural properties

Syntheses of chiral benchrotrene and ferrocene complexes bearing N- protected sulfonimidoyl moieties are reported. They are obtained by metal- catalyzed imination reactions starting from enantiopure sulfoxides. An X-ray structure analysis was carried out for one of the novel complexes confirming the stereospecificity of the imination process.

Asymmetric synthesis of γ-lactones through reaction of sulfoxonium ylides, aldehydes, and ketenes

A method for the enantioselective synthesis of γ-lactones through the reaction of enantioenriched sulfoxonium ylides, aldehydes, and ketenes was developed. Enantioenriched (98% ee) aminosulfoxonium ylide was subjected to reaction with a variety of aldehydes (both aromatic and aliphatic) and disubstituted ketenes, leading to the formation of α,β-substituted γ-lactones in moderate to very good diastereoselectivity (dr up to 95:5) and with enantiomeric excesses of up to 79% ee. Best levels of enantioselectivity were observed in the reactions of enantioenriched aminosulfoxonium ylide with isobutyraldehyde and various alkylarylketenes.

Sulfur-Based Chiral Iodoarenes: An Underexplored Class of Chiral Hypervalent Iodine Reagents

Chiral hypervalent iodine reagents are active players in modern stereoselective organic synthesis. Structurally diverse chiral hypervalent iodine reagents have been synthesised and extensively studied, but hypervalent iodine reagents containing chiral sul

Chiral Dibenzopentalene-Based Conjugated Nanohoops through Stereoselective Synthesis

Conjugated nanohoops allow to investigate the effect of radial conjugation and bending on the involved π-systems. They can possess unexpected optoelectronic properties and their radially oriented π-system makes them attractive for host–guest chemistry. Be

Efficient Synthesis of Sulfur-Stereogenic Sulfoximines via Ru(II)-Catalyzed Enantioselective C-H Functionalization Enabled by Chiral Carboxylic Acid

Ru(II)-catalyzed enantioselective C-H functionalization involving an enantiodetermining C-H cleavage step remains undeveloped. Here we describe a Ru(II)-catalyzed enantioselective C-H activation/annulation of sulfoximines with α-carbonyl sulfoxonium ylides using a novel class of chiral binaphthyl monocarboxylic acids as chiral ligands, which can be easily and modularly prepared from 1,1′-binaphthyl-2,2′-dicarboxylic acid. A broad range of sulfur-stereogenic sulfoximines were prepared in high yields with excellent enantioselectivities (up to 99% yield and 99% ee) via desymmetrization, kinetic resolution, and parallel kinetic resolution. Furthermore, the resolution products can be easily transformed to chiral sulfoxides and key intermediates for kinase inhibitors.

General Method for the Asymmetric Synthesis of N-H Sulfoximines via C-S Bond Formation

A versatile method for the synthesis of enantioenriched N-H sulfoximines is reported. The approach stems from the organomagnesium-mediated ring opening of novel cyclic sulfonimidate templates. The reactions proceed in high yield and with excellent stereofidelity with alkyl, aryl, and heteroaryl Grignard reagents. The chiral auxiliary is readily removed from the resultant sulfoximines via an unusual oxidative debenzylation protocol that utilizes molecular oxygen as the terminal oxidant. This provides a general strategy for the synthesis of highly enantioenriched N-H sulfoximines.

Efficient Kinetic Resolution of Sulfur-Stereogenic Sulfoximines by Exploiting CpXRhIII-Catalyzed C?H Functionalization

Chiral sulfoximines with stereogenic sulfur atoms are promising motifs in drug discovery. We report an efficient method to access chiral sulfoximines through a C?H functionalization based kinetic resolution. A rhodium(III) complex equipped with a chiral Cpx ligand selectively participates in conjunction with phthaloyl phenylalanine in the C?H activation of just one of the two sulfoximine enantiomers. The intermediate reacts with various diazo compounds, providing access to chiral 1,2-benzothiazines with synthetically valuable substitution patterns. Both sulfoximines and 1,2-benzothiazines were obtained in high yields and excellent enantioselectivity, with s-values of up to 200. The utility of the method is illustrated by the synthesis of the key intermediates of two pharmacologically relevant kinase inhibitors.

Enantiopure sulfoximines-catalyzed 1, 4-additions to 2-en-ketone

An efficient chiral catalyst procedure for the preparation of β-chiral ketone via the 1, 4-additions reaction of 2-en-ketone has been developed using enantiopure sulfoximines modified with functional groups as ligands. The carefully design and synthesized

Iron(II)-Catalyzed Direct Synthesis of NH Sulfoximines from Sulfoxides

Free NH-sulfoximines were directly prepared from sulfoxides through iron catalysis by applying a readily available, shelf-stable hydroxylamine triflic acid salt. No additional oxidant is needed, and the substrate scope is broad, including a range of heter