33830-24-9

Upstream product

• 286-20-4 cyclohexane-1,2-epoxide 
• 73391-84-1 sodium 1,3-diphenyl-2-azapropenide 
• 106112-48-5 trans-2-<1-(phenylthio)benzyl>cyclohexanol 
• 169892-12-0 (5E)-7-oxo-7-phenyl-hept-5-enal 
• 88773-76-6 7-oxo-7-phenyl-heptanal 
• 100-47-0 benzonitrile 
• 111-30-8 Glutaraldehyde 

Downstream Products

• 1114462-94-0 C₁₃H₁₆O₂ 
• 870707-25-8 (1R,2R)-2-benzoylcyclohexanol 

Relevant academic research and scientific papers

Synthesis of carbocycles by enone-selective reduction using organoiodotin hydride

By using di-n-butyliodotin hydride (n-Bu2SnIH), carbocycles were prepared from substrates bearing both enone and formyl moieties, where the enone-selective reduction was followed by a diastereoselective intramolecular aldol reaction. (C) 2000 Elsevier Science Ltd.

Titanocene-promoted intermolecular couplings of epoxides with nitriles. An easy access to β-hydroxyketones

(Chemical Equation Presented) Radical couplings of epoxides and nitriles mediated by Cp2TiCl provide a diastereoselective route to the synthesis of β-hydroxyketones. The conditions of this "aldol- like" reaction are mild enough to avoid the dehydration of the β-hydroxyketone. The scope of the coupling reaction with functionalized and tetrasubstituted epoxides has been studied. The radical character of the coupling reactions is demonstrated.

TBD-catalyzed direct 5- and 6-enolexo aldolization of ketoaldehydes

Treatment of unfunctionalized acyclic ketoaldehydes with a catalytic amount of 1,5,7-triazabicyclo[4.4.0]dec-5-ene induces a direct intramolecular 5- and 6-enolexo aldolization, furnishing 2-ketocyclopentanols and 2-ketocyclohexanols in good-to-excellent yields. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Indium(III) acetate-catalyzed 1,4-reduction and reductive aldol reactions of α-enones with phenylsilane

A catalytic amount of In(OAc)3 smoothly promoted 1,4-reduction of certain α-enones with PhSiH3 in ethanol at ambient temperature. The intermediary enolates could be used for inter- and intramolecular aldol reactions and intramolecular Michael addition.

Selective 1,4-reduction of unsaturated carbonyl compounds using Co2(CO)8-H2O

α,β-Unsaturated ketones and aldehydes were selectively reduced to the corresponding saturated carbonyl compounds by Co2(CO)8-H2O system. The current reducing system also offered a chemoselective reduction of less substituted unsaturated carbonyl groups.

Reductive generation of enolates from enones using elemental hydrogen: Catalytic C-C bond formation under hydrogenative conditions

Exposure of enones to elemental hydrogen in the presence of a Rh(I) catalyst enables reductive enolate generation, as evidenced by electrophilic trapping of the enolate by appendant and exogenous aldehyde partners. The significance of these findings resides in the ability to regioselectivity generate and transform transition metal enolates under catalytic conditions that circumvent formation of stoichiometric byproducts. Copyright

Diastereoselective cycloreductions and cycloadditions catalyzed by Co(dpm)2-silane (dpm = 2,2,6,6-tetramethylheptane-3,5-dionate): Mechanism and partitioning of hydrometallative versus anion radical pathways

In the presence of phenylsilane and 5 mol % cobalt(II) bis(2,2,6,6-tetramethylheptane-3,5-dionate), aryl-substituted monoenone monoaldehydes and bis(enones) undergo reductive cyclization to afford synaldol and anti-Michael products, respectively. For both

Stereoselective Ring Opening Reaction of 2-cycloalkanols Mediated by N-Chlorosuccinimide and Triethylamine

Treatment of 2-cyclohexanol (2c) with N-chlorosuccinimide (NCS) and triethylamine gave various product 3-6c depending on reaction conditions.Exclusive ring-opening reaction of 2c was achieved by temperature control.Thus, five-, six-, and seven-membered cycloalkanols 2a-g were converted to ω-oxo-α,β-unsaturated sulfides 6a-g in good yields.The stereochemistry of the reaction was determined by using four diastereomers 10a-d; trans-erythro-10b and cis-threo-10c afforded (E)- and (Z)-heptenals 6c as a single isomer, respectively, while a mixture of the two isomers 6c (60:40 or 40:60) was obtained from trans-threo-10a and cis-erythro-10d.Allyl-, propargyl-, and cyclohexanols 23, 25, and 27 also yielded corresponding unsaturated sulfides 24, 26, and 28.

The Reaction of Sodium 1,3-Diphenyl-2-azapropenide with 1,2-Epoxycyclohexane

Ring opening of 1,2-epoxycyclohexane by the title aza-allylic anion afforded a mixture of anions, the quenching and subsequent hydrolysis of which gave rise to trans-2-(α-aminobenzyl)cyclohexanol (10) and benzylamine as the basic fraction, and to either 1-benzoylcyclohexene (11) or trans-2-benzoylcyclohexanol (12), cis-2-benzoylcyclohexanol (14), and benzaldehyde as the neutral fraction: the type of ketone obtained depended upon the hydrolytic conditions.The perhydrobenzoxazine (7) was shown to be the precursor of compound (10).Sodium 1,3-diphenyl-2-azapropenide thus behaved both as an α-benzylamine carbanion equivalent and as a benzoyl anion equivalent.