32121-04-3

Upstream product

• 104-55-2 3-phenyl-propenal 
• 4104-47-6 N-sulfinyl-p-toluenesulfonamide 
• 19752-27-3 phenylallyl(tributyl)stannane 
• 55962-05-5 4-methyl-N-[(E)-phenyl-λ³-iodanylidene]benzenesulfonamide 
• 936011-91-5 (S)-2-phenyl-1-tosylazetidine 
• 104-54-1 3-Phenylpropenol 
• 70-55-3 toluene-4-sulfonamide 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 2327-99-3 1-phenylpropadiene 
• 4392-24-9 Cinnamyl bromide 
• 32120-97-1 ethyl cinnamyl(tosyl)carbamate 
• 71535-50-7 (S)-(+)-2-benzyl-1-(p-tolylsulfonyl)aziridine 
• 4335-60-8 (E)-cinnamylamine 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 5435-02-9 4-methyl-N-(3-phenylpropyl)benzenesulfonamide 
• 79807-34-4 N-(3-phenyl-propyl)-N-(toluene-4-sulfonyl)-glycine 
• 79807-47-9 N-(3-phenylprop-2-enyl)-N-tosylglycine 
• 113984-52-4 3-cinnamylpentane-2,4-dione 
• 1393608-08-6 2-bromo-2-methyl-N-[(4-methylphenyl)sulfonyl]-N-2-cinnamylpropanamide 
• 86553-38-0 1-[(4-methylphenyl)sulfonyl]-2-benzylpyrrolidine 
• 1334688-33-3 4-methyl-N-(3-phenyl-allyl)-N-(3-phenylprop-2-ynyl)benzenesulfonamide 
• 1598431-81-2 4-methyl-N-((3-phenyloxiran-2-yl)methyl)-N-(3-phenylprop-2-yn-1-yl)benzenesulfonamide 
• 1598431-83-4 4-methyl-N-((3-phenyloxiran-2-yl)methyl)-N-(3-(p-tolyl)prop-2-yn-1-yl)benzenesulfonamide 
• 1598431-51-6 phenyl(4-phenyl-1-tosyl-3,4-dehydropiperidin-3-yl)methanone 
• 1598431-53-8 (4-phenyl-1-tosyl-3,4-dehydropiperidin-3-yl)(p-tolyl)methanone 

Relevant academic research and scientific papers

High Chirality Transfer in Chiral Selenimides via Sigmatropic Rearrangement

The imination of chiral cinnamyl 2-(1-dimethylaminoethyl)ferrocenyl selenides with phenyliodinane and chloramine-T affords the corresponding chiral allylic amines via sigmatropic rearrangement of the selenimide intermediates with up to 87percent ee, highly diastereoselective imination of selenides and highly stereospecific sigmatropic rearrangement being shown.

Amine compound as well as preparation method and application thereof

The invention discloses an amine compound containing allyl or benzyl as well as a preparation method and application of the amine compound. The preparation method comprises the steps of sequentially adding a raw material 1, amine, a catalyst and an additive into a reaction solvent, and stirring and reacting for 12-24 hours in an air atmosphere at the temperature of 50-120 DEG C to obtain a reaction solution, wherein the raw material 1 is allyl alcohol or benzyl alcohol, and the molar volume ratio of the raw material 1 to the amine to the catalyst to the additive to the reaction solvent is (0.2 to 8) mmol: (0.4 to 12) mmol: (0.01 to 0.4) mmol: (0.01 to 0.4) mmol: (2 to 40) mL; and removing the reaction solvent of the reaction solution, and then carrying out purification through thin layer chromatography/column chromatography, wherein a developing solvent system is petroleum ether/ethyl acetate, and the amine compound containing allyl or benzyl is obtained. The amine compound can be applied to preparation of framework of biological and pharmaceutical active molecules. The preparation method disclosed by the invention is wide in applicable substrate range, convenient to operate, green and environment-friendly.

Copper(I)-Catalyzed Enyne Oxidation/Cyclopropanation: Divergent and Enantioselective Synthesis of Cyclopropanes

An efficient copper(I)-catalyzed enyne oxidation/cyclopropanation for the modular synthesis of cyclopropane derivatives is described, which represents the first non-noble metal-catalyzed enynes oxidation/cyclopropanation by the in situ generated α-oxo copper carbenes. This protocol allows the assembly of valuable cyclopropane-γ-lactams in generally good to excellent yields with excellent diastereoselectivity. More significantly, the enantioselective version of enyne oxidation/cyclopropanation has been disclosed with chiral copper catalysts.

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.).

Lewis Base-Catalyzed Amino-Acylation of Arylallenes via C-N Bond Cleavage: Reaction Development and Mechanistic Studies

Lewis base-catalyzed transformations of allenes have received much attention over the last decades. However, this type of reaction has so far been limited to activated allenes bearing an electron-withdrawing group. On the other hand, cleavage of an amide C-N bond to forge other chemical bonds has been widely reported but restricted to low atom economy due to the waste of the amine moiety of amides. We initiated a project of metal-catalyzed amino-acylation of allenes via cleavage of amide C-N bonds. Surprisingly, an amino-acylation of weakly activated aryl allenes was discovered via Lewis base catalysis, providing 2-methyl-3-aroylindole products, "privileged structures"in drug discovery. This is a unique example of Lewis base catalysis of weakly activated allenes, which was not reported yet. Extensive experimental and computational studies have been conducted to provide insight into the reaction mechanism. The nucleophilic addition of Lewis base catalyst to aryl allene is the rate-limiting step. A challenging [1,3]-proton transfer is realized by nitrogen anion intermediate assisted sequential [1,4]- and [1,6]-proton transfer in the reaction pathway.

Arene Trifunctionalization with Highly Fused Ring Systems through a Domino Aryne Nucleophilic and Diels–Alder Cascade

A convenient and efficient domino aryne process was developed under transition-metal-free conditions to generate a range of tetra- and pentacyclic ring systems. This transformation was realized via a 1,2-benzdiyne through a nucleophilic and Diels–Alder reaction cascade using styrene as the diene moiety. Three new chemical bonds, namely one C?N and two C?C bonds, and two benzofused rings could be constructed concomitantly, which was made possible by distinct chemoselective control at both the 1,2-aryne and 2,3-aryne stages. Moreover, in-depth studies were carried out on the domino aryne precursors and controlling the diastereoselectivity.

Visible photocatalysis of novel oxime phosphonates: Synthesis of β-aminophosphonates

A novel type of oxime phosphonate was synthesized and used in the intermolecular cascade radical addition reaction of alkenes to access β-aminophosphonates via visible-light-driven N-centered iminyl radical-mediated and redox-neutral selective C-P single-bond cleavage in an active phosphorus radical route. The procedure is characterized by its ability to achieve the construction of Csp3-P and Csp3-N bonds without the requirement for oxidants and bases.

Regioselective Cp*Ir(III)-Catalyzed Allylic C-H Sulfamidation of Allylbenzene Derivatives

In this study we report the development of the regioselective Cp*Ir(III)-catalyzed allylic C-H sulfamidation of allylbenzene derivatives, using azides as the nitrogen source. The reaction putatively proceeds through a Cp*Ir(III)-π-allyl intermediate and demonstrates exclusive regioselectivity for the branched position of the π-allyl. The reaction performs well on electron-rich and electron-deficient allylbenzene derivatives and is tolerant of a wide range of functional groups, including carbamates, esters, and ketones. The proposed mechanism for this reaction proceeds via C-N reductive elimination from a Cp*Ir(V) nitrenoid complex at the branched position of the π-allyl.

Synthesis of Diverse Boron-Handled N-Heterocycles via Radical Borylative Cyclization of N-Allylcyanamides

A synthetic method based on radical borylation/cyclization cascades of N-allylcyanamides was developed to construct diverse boron-substituted N-heterocycles. In the reaction process, the N-heterocyclic carbene-boryl radical underwent a chemo- and regiosel

Unprecedented nucleophile-promoted 1,7-S or Se shift reactions under Pummerer reaction conditions of 4-alkenyl-3-sulfinylmethylpyrroles

A unique 1,7-S- and Se-shift reaction under Pummerer reaction conditions of 4-alkenyl-3-sulfinyl- and seleninylpyrroles was described. The usual Pummerer reaction of 4-(alkenylaminomethyl)-3-phenylsulfinylpyrroles and a successive reaction with tetrabutyl