18621-79-9

Upstream product

• 169892-12-0 (5E)-7-oxo-7-phenyl-hept-5-enal 
• 88773-76-6 7-oxo-7-phenyl-heptanal 
• 111-30-8 Glutaraldehyde 
• 106112-48-5 trans-2-<1-(phenylthio)benzyl>cyclohexanol 
• 286-20-4 cyclohexane-1,2-epoxide 
• 73391-84-1 sodium 1,3-diphenyl-2-azapropenide 
• 3580-38-9 2-Benzoylcyclohexanone 
• 100-47-0 benzonitrile 

Downstream Products

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

Relevant academic research and scientific papers

Synthesis of new chiral keto alcohols by baker's yeast

Fourteen chiral α- and β-keto alcohols 2a-2r were synthesized by the asymmetric reduction of their corresponding diketones 1a-1r via baker's yeast. In addition, ten corresponding racemic α-keto alcohols were synthesized by the benzoin condensation of their corresponding aldehydes, which were used for the determination of the ee values through their chiral resolution on chiral HPLC. Amongst the 15 diketones, 1j and chiral α-keto alcohols 2i, 2j and chiral β-keto alcohol 2r are novel compounds. Six keto alcohols 2b, 2c, 2d, 2f, 2h and 2p were synthesized by baker's yeast for the first time. There are some studies in the literature where baker's yeast was applied to the diketones 1a, 1g, 1e, 1k and 1n under various conditions different to those reported herein. The yields and the ee values of these studies were not as high as ours. All of the keto alcohols synthesized were characterized by IR, NMR (1H and 13C), and MS. The relationship between the structure of the diketone and the yield, diastereoselectivity and enantiomeric excess is also discussed.

Synthesis of chiral 2-aroyl-1-tetralols: Asymmetric transfer hydrgenation of 2-aroyl-1-tetralones via dynamic kinetic resolution

The dynamic kinetic resolution of 2-aroyl-1-tetralones was achieved via asymmetric transfer hydrogenation using (S,S)-RuCl(p-cymene)TsDPEN (TsDPEN=N-(tosyl)-1,2-diphenylethylenediamine) in formic acid/triethyl- amine (5:2, molar ratio), afforded the desired products in good yields (up to 85%) with diastereomeric ratio up to >99:1 and high enantiomeric excesses (up to >99%). The absolute configuration of major the product was confirmed by X-ray crystal structure analysis. Copyright

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.

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

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

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.