17540-15-7

Upstream product

• 99942-90-2 2-Acetoxy-1-phenyl-cyclohexanol 
• 4829-01-0 (1R,2R)-1-phenyl-1-cyclohexene oxide 
• 771-98-2 1-Phenylcyclohexene 
• 4829-01-0 (-)-(1S,2S)-1-phenylcyclohex-1-ene oxide 
• 5775-23-5 1-phenylcyclohexene oxide 
• 4829-02-1 2-hydroxy-2-phenylcyclohexanone 
• 23313-45-3 acetic acid 2-acetoxy-2-phenylcyclohexyl ester 
• 1222099-34-4 (+/-)-2-(2-tolylaminooxy)cyclohexanone 
• 100-58-3 phenylmagnesium bromide 
• 27167-34-6 trans-1-Phenylcyclohexane-1,2-diol 
• 1161819-40-4 (R)-2-(2-tolylaminooxy)cyclohexanone 
• 4912-59-8 1-phenyl-1,2-cyclohexanediol 
• 23313-43-1 cis-acetic acid 2-hydroxy-2-phenyl-cyclohexyl ester 

Downstream Products

• 134750-73-5 (-)-cis-2-(Methoxymethoxy)-1-phenylcyclohexanol 
• 134750-77-9 (-)-cis-4a-Phenyloctahydro-5,8,11,14,17,20-hexaoxabenzocyclooctadecane 
• 98919-68-7 (1R,2S)-trans-2-phenylcyclohexanol 
• 4829-02-1 (S)-(+)-2-hydroxy-2-phenylcyclohexanone 
• 134780-72-6 (1R,2S)-2-Methoxymethoxy-1-phenyl-cyclohexanol 
• 1444-65-1 (RS)-2-phenylcyclohexanone 
• 4912-59-8 (1R,2R)-1-phenyl-1,2-cyclohexanediol 
• 134750-78-0 (-)-trans-4a,20a-Diphenyloctahydro-5,8,11,14,17,20-hexaoxabenzocyclooctadecane 
• 134875-74-4 (-)-trans-1,2-diphenylcyclohexane-1,2-diol 
• 134750-75-7 2,2'-Oxydiethylenedioxybis(2-phenylcyclohexanol) 
• 134750-74-6 (+)-2,2'-Oxydiethylenedioxybis(2-phenylcyclophenylethyl methyl ether) 
• 27167-34-6 trans-1-Phenylcyclohexane-1,2-diol 

Relevant academic research and scientific papers

Photo-Induced Dihydroxylation of Alkenes with Diacetyl, Oxygen, and Water

Herein reported is a photo-induced production of vicinal diols from alkenes under mild reaction conditions. The present dihydroxylation method using diacetyl (= butane-2,3-dione), oxygen, and water dispenses with toxic reagents and intractable waste generation.

Racemic or enantioselective osmium-catalyzed dihydroxylation of olefins under near-neutral conditions

K3Fe(CN)6 and NaIO4 serve as catalytic co-oxidants for osmium-catalyzed dihydroxylations that are performed under near-neutral conditions with K2S2O8 as the stoichiometric oxidant and Na2HPO4 as the base. By using either quinuclidine or hydroquinidine 1,4-phthalazinediyl ether [(DHQD)2Phal], good yields of racemic or enantioenriched diols are obtained. This simple, biphasic procedure offers advantages over other neutral dihydroxylation protocols that use N-methylmorpholine oxide as the stoichiometric oxidant, by suppressing the secondary catalytic cycle that leads to reduced enantioselectivities. The utility of the procedure, which is nicely suited for base-labile starting materials or products, is demonstrated by performing the dihydroxylation in the presence of an aliphatic aldehyde moiety.

Enantioselective Dihydroxylation of Alkenes Catalyzed by 1,4-Bis(9-O-dihydroquinidinyl)phthalazine-Modified Binaphthyl–Osmium Nanoparticles

A series of unprecedented binaphthyl–osmium nanoparticles (OsNPs) with chiral modifiers were applied in the heterogeneous asymmetric dihydroxylation of alkenes. A remarkable size effect of the OsNPs, depending on the density of the covalent organic shells, on the reactivity and enantioselectivity of the dihydroxylation reaction was revealed. Successful recycling of the OsNPs was also demonstrated and high reaction efficiency and enantioselectivity were maintained.

Bronsted Acid Mediated Direct α-Hydroxylation of Cyclic α-Branched Ketones

We report a Bronsted acid mediated direct α-hydroxylation of cyclic α-branched ketones via a tandem aminoxylation/N-O bond-cleavage process. Nitrosobenzene is used as the oxidant and subsequently promotes the liberation of the free alcohol. The desired pr

Green Organocatalytic Dihydroxylation of Alkenes

An inexpensive, green, metal-free one-pot procedure for the dihydroxylation of alkenes is described. H2O2 and 2,2,2-trifluoroacetophenone were employed as the oxidant and organocatalyst, respectively, in this highly sustainable protocol in which a variety of homoallylic alcohols, aminoalkenes, and simple alkenes were converted into the corresponding polyalcohols in good to excellent yields. This process takes advantage of an epoxidation reaction followed by an acidic treatment in which water participates in the ring opening of the in situ prepared epoxide to lead to the desired product.

Osmium on chelate resin: Nonvolatile catalyst for the synthesis of DIOLS from alkenes

Osmium tetraoxide (OsO4) was immobilized on a commercially available chelate resin DIAION CR11 (CR11) just by simply immersing it in a methanol solution of OsO4 at room temperature. The resulting purple solid, 5% Os/CR11, indicated no volatility, and effectively catalyzed the oxidation of various alkenes to the corresponding diols.

Novel biphenyl organocatalysts for iminium ion-catalyzed asymmetric epoxidation

Two novel chiral biphenyl iminium salts derived from L-acetonamine, containing electron-withdrawing 3,30-substituents on the biphenyl unit, have been prepared and tested as asymmetric catalysts for epoxidation of prochiral alkenes. The results are compared with those achieved using the corresponding unsubstituted system.

Enantioselective titanium(III)-catalyzed reductive cyclization of ketonitriles

Reduction, please! The title reaction affords ?-hydroxyketones, a common structural motif in biologically active natural products, in good yields and high enantioselectivities at room temperature. The commercially available ansa-titanocene 1 was found to be an efficient catalyst for this process, which presumably proceeds by addition of a ketyl radical to a nitrile.

Synthesis and reaction of phthaloyl peroxide derivatives, potential organocatalysts for the stereospecific dihydroxylation of alkenes

To improve the synthesis and reactivity of phthaloyl peroxide derivatives a method has been developed using sodium percarbonate and phthaloyl chlorides. The reactions of the new phthaloyl peroxide derivatives with trans-stillbene as well as the improved reactivity of 3,4-dichlorophthaloyl peroxide with a variety of alkenes are reported.

The nature of the catalytically active species in olefin dioxygenation with PhI(OAc)2: Metal or proton?

Evidence for the protiocatalytic nature of the diacetoxylation of alkenes using PhI(OAc)2 as oxidant is presented. Systematic studies into the catalytic activity in the presence of proton-trapping and metal-complexing agents indicate that protons act as catalysts in the reaction. Using triflic acid as catalyst, the selectivity and reaction rate of the conversion is similar or superior to most efficient metal-based catalysts. Metal cations, such as Pd(II) and Cu(II), may interact with the oxidant in the initiation phase of the catalytic transformation; however, 1 equiv of strong acid is produced in the first cycle which then functions as the active catalyst. Based on a kinetic study as well as in situ mass spectrometry, a mechanistic cycle for the proton-catalyzed reaction, which is consistent with all experimental data presented in this work, is proposed.