5682-61-1

Upstream product

• 186581-53-3 diazomethane 
• 939-89-9 (1S)-2-phenylcyclopropane-1-carboxylic acid 
• 48126-51-8 (1R,2S)-2-phenylcyclopropane-1-carboxylic acid 
• 23020-18-0 (1S,2R)-2-phenylcyclopropanecarboxylic acid 
• 23020-15-7 (1S,2S)-2-phenylcyclopropane-1-carboxylic acid 
• 67-56-1 methanol 
• 939-87-7 (1SR,2SR)-2-phenylcyclopropanecarbonyl chloride 
• 939-90-2 trans-2-phenylcyclopropane-1-carboxylic acid 
• 100-42-5 styrene 
• 623-73-4 diazoacetic acid ethyl ester 
• 1205000-67-4 (+)-trans-2,2-dibromo-3-phenylcyclopropanecarboxylic acid methyl ester 
• 100-39-0 benzyl bromide 
• 292638-85-8 acrylic acid methyl ester 
• 103-26-4 Methyl cinnamate 

Downstream Products

• 110659-52-4 (1'R,2'S)-1-(2'-methylcyclopropyl)-2-nitrobenzene 
• 110659-53-5 (+)-(1'R,2'S)-2-(2'-methylcyclopropyl)aniline 
• 29667-47-8 (+)-(1S,2R)-1-methyl-2-phenylcyclopropane 
• 29667-46-7 (1S,2R)-2-phenylcyclopropylmethanol 
• 110659-48-8 (1'S,2'S)-1-(2'-methylcyclopropyl)-2-nitrobenzene 
• 110659-49-9 (+)-(1'S,2'S)-2-(2'-methylcyclopropyl)aniline 
• 53403-04-6 (+)-(1S,2S)-1-methyl-2-phenylcyclopropane 
• 110659-58-0 (1S,2S)-trans-1-(hydroxymethyl)-2-phenylcyclopropane 

Relevant academic research and scientific papers

Electrochemical Ring-Opening Dicarboxylation of Strained Carbon-Carbon Single Bonds with CO2: Facile Synthesis of Diacids and Derivatization into Polyesters

Diacids are important monomers in the polymer industry to construct valuable materials. Dicarboxylation of unsaturated bonds, such as alkenes and alkynes, with CO2 has been demonstrated as a promising synthetic method. However, dicarboxylation of C-C single bonds with CO2 has rarely been investigated. Herein we report a novel electrochemical ring-opening dicarboxylation of C-C single bonds in strained rings with CO2. Structurally diverse glutaric acid and adipic acid derivatives were synthesized from substituted cyclopropanes and cyclobutanes in moderate to high yields. In contrast to oxidative ring openings, this is also the first realization of an electroreductive ring-opening reaction of strained rings, including commercialized ones. Control experiments suggested that radical anions and carbanions might be the key intermediates in this reaction. Moreover, this process features high step and atom economy, mild reaction conditions (1 atm, room temperature), good chemoselectivity and functional group tolerance, low electrolyte concentration, and easy derivatization of the products. Furthermore, we conducted polymerization of the corresponding diesters with diols to obtain a potential UV-shielding material with a self-healing function and a fluorine-containing polyester, whose performance tests showed promising applications.

Boronic Acid-Mediated Photocatalysis Enables the Intramolecular Hydroacylation of Olefins Using Carboxylic Acids

An intramolecular hydroacylation of olefins using carboxylic acids (CAs) has been developed. With the aid of a boronic acid, CAs can be used as acyl-radical precursors in catalytic photoredox reactions driven by visible light. The CAs are easily converted into their corresponding cyclic ketones without the need to use any stoichiometric activating reagents. Mechanistic studies implied that the formation of an “ate” complex from the CA and boronic acid is crucial for the generation of the acyl radical equivalent from the unreactive carboxy group.

Green Esterification of Carboxylic Acids Promoted by tert-Butyl Nitrite

In this work, the green esterification of carboxylic acids promoted by tert-butyl nitrite has been well developed. This transformation is compatible with a broad range of substrates and exhibits excellent functional group tolerance. Various drugs and substituted amino acids are applicable to this reaction under near neutral conditions, with good to excellent yields.

Synthesis of a novel C2-symmetric bis-oxazoline (=bis[4,5-dihydrooxazole]) and its application as chiral ligand in asymmetric transition metal catalysis

The new C2-symmetric bis-oxazoline (=bis[4,5-dihydrooxazole]) 2 with a chiral trans-(2R,3R)-2,3-bis(3,5-diphenylphenyl)cyclopropylidene (=trans-(2R,3R)-2,3-bis([1,1′: 3′,1″-terphenyl]-5′-yl) cyclopropylidene) backbone was efficiently synthesized (Scheme). All synthetic steps were easy to perform and led to the desired product in good overall yields. Compound 2 was tested and compared as ligand in several enantioselective catalytic reactions such as palladium(0)-catalyzed enantioselective allylic alkylations and copper(I)-catalyzed enantioselective cyclopropanations and aziridinations. Copyright

Novel trans-2-aryl-cyclopropylamine analogues as potent and selective dipeptidyl peptidase IV inhibitors

A series of trans-2-aryl-cyclopropylamine derived compounds were synthesized and evaluated their biological activities against DPP-IV. The structure-activity relationships (SAR) led to the discovery of novel series of DPP-IV inhibitors, having IC50 values of 100 nM with excellent selectivity over the closely related enzymes, DPP8, DPP-II and FAP. The studies identified a potent and selective DPP-IV inhibitor 24b, which exhibited the ability to both significantly inhibit plasma DPP-IV activity in rats and improve glucose tolerance in lean mice and diet induced obese mice.

Stereo- and regiocontrol in ene-dimerisation and trimerisation of 1-trimethylsilyl-3-phenylcyclopropene

1-Trimethylsilyl-3-phenylcyclopropene and its 2D-analog undergo a highly stereocontrolled ene-reaction to give a single dimer. Further reaction leads to one or more trimers derived through two ene-reactions. The dimer formed easily undergoes cycloaddition

Efficient syntheses of four stable-isotope labeled (1R)-menthyl (1S,2S)-(+)-2-phenylcyclopropanecarboxylates

Many carbenoid cyclopropanation reactions promoted by chiral catalysts give product mixtures reflecting impressive diastereo- and enantioselectivities. Few provide a single chiral product efficiently. This limitation has been overcome in cyclopropanations of styrene and isotopically labeled styrenes with α-diazoacetates. Convenient syntheses on a 20 g scale of each of four chiral isotopically labeled (1R)-menthyl (1S,2S)-2- phenylcyclopropanecarboxylates (the 1-d-3-13C, 1,(3S)-d2, 1,2,(3S)-d3, and 1,3,3-d3 isotopomers) of better than 99% ee have been realized. The Royal Society of Chemistry 2006.

Synthesis of polymer bound azabis(oxazoline) ligands and their application in asymmetric cyclopropanations

Aza(bisoxazoline) ligands were attached to various polymeric supports and the resulting immobilized ligands were evaluated in copper(I)-catalyzed asymmetric cyclopropanations. The efficiency of these transformations depends greatly on the polymeric support, on the protocol being applied for the immobilization of the ligands, and on the preparation of the catalysts.

A practical and controllable enantioselective synthesis of 2-phenyl-1-cyclopropanecarboxylates via a camphor-derived sulfonium ylide

We have developed a practical and controllable enantioselective synthesis of 2-phenyl-1-cyclopropane-carboxylates via camphor-derived sulfonium ylide. The procedure has many advantages such as cheap starting materials, facile synthetic procedures, good yields, excellent diastereoselectivities and high enantioselectivities. Georg Thieme Verlag Stuttgart.

Bis(oxazoline)·copper(I)-catalyzed enantioselective cyclopropanation of cinnamate esters with diazomethane

Chiral bis(oxazoline)-copper(I) complexes were found to be effective catalysts for the enantioselective cyclopropanation reaction of trans-cinnamate esters exploiting an argon flow mediated diazomethane addition method. After optimization of the catalyst structure, good yields and enantiomeric excesses were obtained with electron-poor methyl cinnamate derivatives. Sterically demanding esters gave lower yields and enantioselectivities. The correlation between the product enantiopurities and the σ+ values of the aromatic para-substituents was shown to be linear in a Hammet-type plot.