38455-36-6

Upstream product

• 24395-14-0 N-(p-tolylsulfonyl)-2-phenylaziridine 
• 70775-39-2 dimethylsulfoxonium methylide 
• 58567-43-4 4-methyl-N-(1-phenyl-allyl)-benzenesulfonamide 
• 51608-60-7 N-(benzylidene)-p-methylbenzenesulfonamide 
• 100-42-5 styrene 
• 127-65-1 chloroamine-T 
• 14593-04-5 3-amino-3-phenyl-1-propanol 
• 98-59-9 p-toluenesulfonyl chloride 
• 101719-48-6 ethyl 3-(4-methylphenylsulfonamido)-3-phenylpropanoate 
• 155496-06-3 (+/-)-3-phenyl-3-(toluene-4-sulfonylamino)-propionic acid 
• 70-55-3 toluene-4-sulfonamide 
• 100-52-7 benzaldehyde 
• 473-34-7 N,N-dichloro-p-toluenesulfonamide 
• 155495-87-7 tert-butyl 3-(4-toluenesulfonamido)-3-phenylpropanoate 

Downstream Products

• 824390-97-8 2,4-diphenyl-1-(toluene-4-sulfonyl)-1,4,5,6-tetrahydropyrimidine 
• 137401-51-5 3-phenyl-N-tosylhexa-4,5-dienylamine 
• 884844-42-2 N-(3-cyclopent-2-enyl-3-phenyl-propyl)-4-methyl-benzenesulfonamide 
• 1199800-55-9 8-methyl-2-phenyl-5-tosyl-3,4,5,8-tetrahydro-2H-1,5-oxazocine 

Relevant academic research and scientific papers

Palladium-Catalyzed Regioselective and Stereospecific Ring-Opening Suzuki-Miyaura Arylative Cross-Coupling of 2-Arylazetidines with Arylboronic Acids

We have developed a palladium-catalyzed regioselective and enantiospecific ring-opening Suzuki–Miyaura arylative cross-coupling of N-tosyl-2-arylazetidines to give enantioenriched 3,3-diarylpropylamines. This reaction represents an example of transition-metal-catalyzed ring-opening cross-coupling using azetidines as a non-classical alkyl electrophile. Density functional theory rationalized the mechanism of the full catalytic cycle, which consists of the selectivity-determining ring opening of the azetidine, reaction with water, rate-determining transmetalation, and reductive elimination. Transition states of the selectivity-determining ring-opening step were systematically determined by the multi-component artificial force induced reaction (MC-AFIR) method to explain the regioselectivity of the reaction. (Figure presented.).

Branched Amine Synthesis via Aziridine or Azetidine Opening with Organotrifluoroborates by Cooperative Br?nsted/Lewis Acid Catalysis: An Acid-Dependent Divergent Mechanism

A practical catalytic method to synthesize β,β- and γ,γ-substituted amines by opening aziridines and azetidines, respectively, using alkenyl, alkynyl, or aryl/heteroaryl trifluoroborate salts is described. This reaction features simple open-flask reaction conditions, the use of transition-metal-free catalysis, complete regioselectivity, and high diastereoselectivity. Preliminary mechanistic studies suggest that carbocation formation is disfavored. Stereoretentive addition is favored with Br?nsted acid present, while stereoinversion is favored in its absence, indicating divergent mechanisms.

Stereoselective synthesis of activated 2-arylazetidines via imino-aldol reaction

A simple and efficient synthetic route to substituted N-sulfinyl and N-sulfonyl azetidines is described involving imino-aldol reaction of ester enolates with racemic and non-racemic aldimines for obtaining β-amino esters as a key step. These β-amino ester

Ag(I)-catalyzed regioselective ring-opening of N -tosylaziridine and N -tosylazetidine with S -, O -, and N -nucleophiles and tethered dinucleophiles

[Ag(COD)2]PF6 catalyzes the ring-opening of N-tosylaziridines and -azetidines with alcohols, amines, thiols, and related tethered 1,2-ethane dinucleophiles. Initial rate studies and DFT-based evaluation of stepwise energetics suggest

A convenient synthetic route to 2-aryl-N-tosylazetidines and their ZnX2 (X = I, OTf) mediated regioselective nucleophilic ring opening reactions: synthesis of γ-iodoamines and tetrahydropyrimidines

A general and convenient synthetic route to various 2-aryl-N-tosylazetidines has been described. Their ZnX2 (X = I, OTf) mediated nucleophilic ring opening with halides and [4+2] cycloaddition reactions with various nitriles have been achieved

2-Aryl-N-tosylazetidines as formal 1,4-dipoles for [4 + 2] cycloaddition reactions with nitriles: An easy access to the tetrahydropyrimidine derivatives

(Chemical Equation Presented) A new synthetic route to 2-aryl-N-tosyl azetidines has been developed starting from N-tosylarylaldimines in two steps in an overall yield of 63-70%. A formal [4 + 2] cycloaddition of these 2-aryl-N-tosylazetidines with nitril

Methylene Transfer from Dimethyloxosulphonium Methylide to N-Arylsulphonylaziridines: Stereospecific Synthesis of N-Arylsulphonylazetidines

Several 2-alkyl, 2-aryl-, 2-benzyl-, 2,3-dialkyl- and 2,3-diarylsulphonylazetidines have been prepared in fair to good isolated yields through reaction of N-arylsulphonylaziridines with dimethyloxosulphonium methylide.Fused azetidines, however, could not

Reaction of dimethyloxosulphoniummethylide with oxaziridines - Transformation to azetidines

Reaction of N-arylsulphonyloxaziridines with dimethyloxosulphoniummethylide yields azetidines whereas a similar reaction with N-alkyloxaziridines leads to the corresponding azomethines.

Reaction of Dimethyloxosulphonium Methylide with N-Arylsulphonyl-2-phenylaziridines: a New Synthesis of N-Arylsulphonyl-2-phenylazetidines

Reaction of dimethyloxosulphonium methylide with certain N-arylsulphonyl-2-phenylaziridines, which on heating do not yield azomethine ylides, gives the corresponding azetidines.