3238-03-7

Upstream product

• 108574-35-2 chloro-2 phenyl-1 heptanedione-1,5 
• 91873-49-3 tert-Butyl-((E)-2-chloro-1-phenyl-vinyloxy)-dimethyl-silane 
• 16415-21-7 (2-Benzoyl-vinyl)-triphenylphosphoniumbromid 
• 5633-34-1 (benzoylmethylene)dimethylsulfurane 
• 4070-75-1 1,4-diphenyl-but-2-ene-1,4-dione 
• 21077-81-6 N,N-(dimethylamino)-methylphenylsulfoxonium tetrafluoroborate 
• 959-28-4 1,4-diphenylbut-2-ene-1,4-dione 
• 6263-83-8 1,5-diphenyl-1,5-pentanedione 
• 1774-47-6 trimethylsulfoxonium iodide 
• 768-03-6 Phenyl vinyl ketone 
• 3237-93-2 2,5-diphenyl-3,4-diazanorcaradiene 
• 2873-74-7 gloutaric dichloride 
• 91873-56-2 chloro-2 diphenyl-1,5 pentanedione-1,5 
• 72050-09-0 (E)-3-methoxy-3-phenyl-2-buten-1-ol 

Downstream Products

• 139152-84-4 1,1-Bis(2'-hydroyx-2'-phenylcyclopropyl)methane 
• 184151-87-9 Phenyl(5-phenyl-furan-2-yl)methanone 
• 103269-46-1 1,2,5,5-tetraphenyl-pent-4-en-1-one 
• 808-88-8 (+/-)-trans-1,2-bis-(α-hydroxy-benzhydryl)-cyclopropane 

Relevant academic research and scientific papers

Facile synthesis of libraries of functionalized cyclopropanes and oxiranes using ionic liquids – A new approach to the classical Corey-Chaykovsky reaction

The potential of [PAIM][NTf2]/BMIM-ILs as a base/solvent in the Corey-Chaykovsky reaction is demonstrated by the facile synthesis of libraries of functionalized cyclopropanes from enones and oxiranes from aldehydes and ketones, at room temperature in respectable isolated yields. To demonstrate their application, the synthesized epoxides were employed as substrates for the synthesis of a library of 2,3-disubstituted quinolines, using [BMIM(SO3H)][OTf]/[BMIM][PF6] as a catalyst/solvent. The potential for recycling/reuse of the IL solvents was also explored.

Synthetic studies on a series of functionalized pyrylium salts, 4-chloro- and 4-bromophosphinines

A series of new pyrylium salts that bear sulfonate and phosphonate groups were obtained from the reactions between 2,6-diphenyl-4H-pyran-4-one, sulfonic anhydride, and chlorophosphates, and analyzed spectroscopically. Furthermore, treatment of 2,6-diphenyl-4H-pyran-4-one with phosphoryl chloride or bromide afforded the corresponding 4-chloro- and 4-bromopyrylium tetrafluoroborates in good yield. Subsequently, the synthesis of the corresponding 4-chloro- and 4-bromophosphinines was accomplished by treating the respective chloro- and bromopyrylium tetrafluoroborates with tris(trimethylsilyl)phosphine.

Stereodivergent Rhodium(III)-Catalyzed cis-Cyclopropanation Enabled by Multivariate Optimization

The design of stereodivergent transformations is of great interest to the synthetic community as it allows funneling of a given reaction pathway toward one stereochemical outcome or another by only minor adjustments of the reaction setup. Herein, we present a physical organic approach to invert the sense of induction in diastereoselective cyclopropanation of alkenes with N-enoxyphthalimides through rhodium(III) catalysis. Careful parametrization of catalyst-substrate molecular determinants allowed us to interrogate linear-free energy relationships and establish an intuitive and robust statistical model that correlates an extensive number of data points in high accuracy. Our multivariate correlations-steered mechanistic investigation culminated with a robust and general diastereodivergent cyclopropanation tool where the switch from trans- to cis-diastereoinduction is attributed to a mechanistic dichotomy. Selectivity might be determined by the flexibility of rhodacyclic intermediates derived from ring-opened versus -unopened phthalimides, induced by both their respective ring size and the Sterimol B1 parameter of the CpX ligand on rhodium.

The direct preparation of functionalised cyclopropanes from allylic alcohols or α-hydroxyketones using tandem oxidation processes

New manganese dioxide-mediated tandem oxidation processes (TOPs) have been developed, which facilitate the direct conversion of allylic alcohols and α-hydroxyketones into polysubstituted functionalised cyclopropanes. In the simplest version, the oxidation of an allylic alcohol is carried out in the presence of a stabilised sulfurane, and the intermediate α,β-unsaturated carbonyl compound undergoes in situ cyclopropanation. By using a combination of stabilised phosphorane and sulfurane, the direct conversion of allylic alcohols or α-hydroxyketones into functionalised cyclopropanes is achieved, with in situ cyclopropanation being followed by Wittig olefination, or vice versa. The application of these methods to a formal synthesis of the lignan (±)-picropodophyllone, and to novel analogues of the insecticide allethrin II, is described.

Tandem oxidation processes for the preparation of functionalized cyclopropanes

(Chemical Equation Presented) A novel manganese dioxide-mediated tandem oxidation process (TOP) has been developed which allows the direct conversion of allylic alcohols into cyclopropanes, the intermediate aldehydes being trapped in situ with a stabilized sulfur-ylide. This methodology has been applied successfully to a variety of allylic alcohols and to a formal synthesis of the simple, naturally occurring lignan, (±)-picropodophyllone.

Electrooxidative formation of 1,2-diaroylcyclopropanes from 1,3-diaroylpropanes in the presence of KI

Various 1,2-diaroylcyclopropanes were obtained in good yields by the indirect electrochemical oxidation of 1,3-diaroylpropanes in the presence of catalytic amounts of KI under very mild conditions.

Reaction des vinylogues d'hemiacetals avec les ethers d'enols β-heterosubstitues : nouvelle synthese et cyclisation de composes δ-dicarbonyles α-heterosubstitues

Reaction of hemiacetal vinylogs 1 in the presence of boron trifluoride etherate with silyl enol ethers 2 or 3 prepared from α-heterosubstituted ketones 7 or 9 yields α-halo δ-dicarbonyl compounds 4 (X = Cl, Br) or α-methoxy δ-dicarbonyl compounds 5.When s

SYNTHESE DE COMPOSES DICARBONYLES-1,5 α-HALOGENES UTILISANT DES VINYLOGUES D'HEMIACETALS VOIE D'ACCES A DES CYCLOPROPANES DISUBSTITUES-1,2

Reaction of hemiacetal vinylogs 1 with β-halo silyl enol ethers 2 in the presence of boron trifluoride etherate yields α-halo 1,5-dicarbonyl compounds 3 .Functionalized cyclopropanes 4 are obtained by reaction of diketones 3 in ethanolic potassium hydroxi