33547-94-3

Upstream product

• 2719-27-9 cyclohexanylcarbonyl chloride 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 131292-27-8 (α-cyclohexylcarbonyl-α-ethoxycarbonylmethylene)triphenylphosphorane 
• 60754-49-6 1,1-dibromo-2-cyclohexylethene 
• 541-41-3 chloroformic acid ethyl ester 
• 2043-61-0 cyclohexanecarbaldehyde 
• 64-17-5 ethanol 
• 931-48-6 2-cyclohexylacetylene 
• 201230-82-2 carbon monoxide 

Downstream Products

• 136642-52-9 (Z)-Ethyl 3-cyclohexyl-2-(1-hydroxycyclohexyl)-2-propenoate 
• 136616-89-2 2-[1-Cyclohexyl-meth-(Z)-ylidene]-3-hydroxy-pent-4-enoic acid ethyl ester 
• 136617-01-1 (E)-3-Cyclohexyl-4-hydroxy-hexa-2,5-dienoic acid ethyl ester 
• 136617-00-0 (E)-3,4-Dicyclohexyl-4-hydroxy-but-2-enoic acid ethyl ester 
• 136616-88-1 (Z)-3-Cyclohexyl-2-(cyclohexyl-hydroxy-methyl)-acrylic acid ethyl ester 
• 888039-39-2 ethyl (2E)-3-chloro-3-cyclohexyl-2-iodoacrylate 
• 1009307-09-8 (Z)-ethyl 3-cyclohexyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate 
• 1193381-06-4 (E)-ethyl 3-cyclohexyl-3-p-tolylacrylate 
• 75567-08-7 (E)-3-(1-cyclohexen-1-yl)-2-propenoic acid ethyl ester 
• 1252813-48-1 (S)-ethyl 3-cyclohexyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate 

Relevant academic research and scientific papers

Remote substituent effects in ruthenium-catalyzed [2+2] cycloadditions: An experimental and theoretical study

The effects of a remote substituent on the regioselectivity of ruthenium-catalyzed [2+2] cycloadditions of 2-substituted norbornenes with alkynes have been investigated experimentally and theoretically using density functional theory. Most of the cycloadditions occurred smoothly at room temperature, giving the exo cycloadducts in excellent yields. Regioselectivities of 1.2:1 to 15:1 were observed with various substituents on the C-2 position of the norbornenes. Exo-C-2-substituents usually showed greater remote substituent effects on the regioselectivities of the cycloadditions than the corresponding endo-C-2-substituents. The regioselectivity of the cycloadditions with C-2 substituents containing an exocyclic double bond (sp2 hybridized carbon at C-2) are much higher than the cycloadditions with the exo and endo 2-substituted norbornenes. Theoretical studies predicted the same trends as experiment and matched the experimental product ratios well. The nature of the regioselectivity in this reaction is discussed. Different strengths of the π(C5-C6)→π*(C2-Y) or π(C5-C6)→σ*(C2-Y) orbital interactions in 2-substituted norbornenes result in different degrees of C 5-C6 double bond polarization. Stronger C 5-C6 polarization will increase the difference in the activation energies between the major and minor pathways and thus lead to greater regioselectivities.

An entry to non-racemic β-tertiary-β-amino alcohols, building blocks for the synthesis of aziridine, piperazine, and morpholine scaffolds

A method for the preparation of enantiopure β-tert-amino alcohols bearing a tetrasubstituted C-stereocenter, as well as their conversion into selected medicinally privileged heterocyclic systems (morpholines, aziridines, piperazines) is reported. These co

Efficient Access to Chiral β-Borylated Carboxylic Esters via Rh-Catalyzed Hydrogenation

Rh/bisphosphine?thiourea ligand (ZhaoPhos)-catalyzed asymmetric hydrogenation of (Z)-β-substituted-β-boryl-α,β-unsaturated esters was successfully developed, furnishing a variety of chiral β-borylated carboxylic esters with high yields and excellent enantioselectivities (up to 99% yield and >99% ee). The gram-scale asymmetric hydrogenation was performed efficiently in the presence of only 0.05 mol% (S/C=2 000) catalyst loading with full conversion, 99% yield and 99% ee. Moreover, the hydrogenation product was easily converted to other versatile synthetic intermediates, such as methyl (S)-3-hydroxy-3-phenylpropanoate and methyl (S)-3-(furan-2-yl)-3-phenylpropanoate. (Figure presented.).

Rh-Catalyzed Asymmetric Hydrogenation of β-Substituted-β-thio-α,β-unsaturated Esters: Expeditious Access to Chiral Organic Sulfides

Rh/bifunctional bisphosphine-thiourea ligand (ZhaoPhos)-catalyzed asymmetric hydorgenation of both (Z)- and (E)-isomers of β-substituted-β-thio-α,β-unsaturated esters was successfully developed. This new asymmetric catalytic methodology provided highly efficient access to two enantiomers of chiral organic sulfides ethyl β-substituted-β-thio-propanoates with excellent results (up to 99% yield and >99% ee for (Z)-substrates, up to 99% yield and 98% ee for (E)-substrates, TON up to 5000), which are important intermediates in organic synthesis.

Development of Gold-catalyzed [4+1] and [2+2+1]/[4+2] Annulations between Propiolate Derivatives and Isoxazoles

Two new gold-catalyzed annulations of isoxazoles with propiolates have been developed. Most isoxazoles follow an initial O attack on the alkyne to afford a [4+1] annulation product. This process results in a remarkable alkyne cleavage of initial propiolates. Unsubstituted isoxazoles proceed through an N attack step to yield formal [2+2+1]/[4+2] annulation products. These two annulation products arise initially from two seven-membered heterocyclic intermediates, which then lead to products.

Chemo-, Regio-, and Stereoselective Copper(II)-Catalyzed Boron Addition to Acetylenic Esters and Amides in Aqueous Media

Aqueous conditions were developed for conducting an open-to-air, copper(II)-catalyzed addition of pinBBdan to alkynoates and alkynamides. The simple and mild β-borylation protocol proceeds in a remarkably chemo-, regio-, and stereoselective fashion to aff

Copper(II)-Catalyzed β-Borylation of Acetylenic Esters in Water

A method for the β-borylation of alkynoates has been developed. In the presence of bis(pinacolato)diboron and catalytic amounts of both copper(II) and 4-picoline, substituted alkynoates undergo borylation in a regio-, stereo-, and chemoselective fashion. The reaction is performed under mild conditions using water as solvent and open to the atmosphere to exclusively afford (Z)-β-boryl-α,β-unsaturated esters.

Gold-catalyzed formal [4π+2π]-cycloadditions of tert-butyl propiolates with aldehydes and ketones to form 4H-1,3-dioxine derivatives

Gold-catalyzed formal hetero-[4π+2π] cycloadditions of tert-butyl propiolates with carbonyl compounds proceeded efficiently to yield 4H-1,3-dioxine derivatives over a wide scope of substrates. With acetone as a promoter, gold-catalyzed cycloadditions of these propiolate derivatives with enol ethers led to the formation of atypical [4+2]-cycloadducts with skeletal rearrangement.

Gold-catalyzed 1,2-iminonitronation of electron-deficient alkynes with nitrosoarenes to afford α-imidoyl nitrones

Gold-catalyzed 1,2-iminonitronation of propiolate derivatives with nitrosoarenes to give α-imidoyl nitrones is described; this new reaction is applicable to diverse propiolate derivatives and nitrosoarenes.

Synthesis of α,β-alkynyl esters and unsymmetrical maleate esters catalyzed by pd/c; An efficient phosphine-free catalytic system for oxidative alkoxycarbonylation of terminal alkynes

Pd/C-catalyzed oxidative alkoxycarbonylation of terminal alkynes using alcohols in the presence of tetrabutylammonium iodide under CO/O2 (5:1 atm) has been investigated. The desired α,β-alkynyl esters and unsymmetrical maleate esters are formed in good to excellent yields under different reaction conditions. The present protocol eliminates the use of phosphine ligands and has straightforward catalyst recovery. The catalyst was recycled up to six times without significant loss of catalytic activity. Georg Thieme Verlag Stuttgart . New York.