• Bulletin of the Korean Chemical Society
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• v.8 no.3
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• pp.211-214
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• 1987

Asymmetric reduction of a series of aliphatic ketones and representative other classes of ketones with potassium 9-O-isopinocampheyloxy-9-boratabicyclo[3.3.1]non ane (K 9-O-Ipc-9-BBNH) was studied. All the ketones examined were reduced smoothly to the corresponding alcohols in THF at -$78^{\circ}C$. Thus, the reduction of 2-butanone, 3-methyl-2-butanone, 3,3-dimethyl-2-butanone, 2-octanone, and 4-phenyl-2-butanone provides 51% ee, 61% ee, 44% ee, 35% ee, and 33% ee of optical inductions, respectively. The reduction of other classes of ketones gave 52% ee for 2,2-dimethylcyclopentanone, 47% ee for acetophenone, 23% ee for 3-acetylpyridine, 50% ee for methyl benzoylformate, 4.8% ee for 2-chloroacetophenone, 30% ee for trans-4-phenyl-3-butene-2-one, and 2% ee for 4-phenyl-3-butyn-2-one. Thus, the reagent was found to be most useful in the asymmetric reduction of acyclic and cyclic aliphatic series of ketones.

• Bulletin of the Korean Chemical Society
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• v.8 no.4
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• pp.257-260
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• 1987

The asymmetric reduction of representative prochiral ${\alpha},{\beta}$-acetylenic ketones with a new chiral borohydride reducing agent, potassium 9-0-(1,2: 5,6-Di-O-isopropylidene-${\alpha}$ -D-glucofuranosyl)-9-boratabicyclo[3.3.1]nonane, 1, in THF at $-78^{\circ}C$ was studied. Structurally different acetylenic ketones such as internal ${\alpha},{\beta}$-acetylenic ketones $RC {\equiv} CCOCH_3$ and terminal ${\alpha},{\beta}$-acetylenic ketones $HC {\equiv} CCOR$ were chosen. Thus, the reduction of internal ${\alpha},{\beta}$-acetylenic ketones yields the corresponding propargyl alcohols, such as 67% ee for 3-hexyn-2-one, 75% ee for 5-methyl-3-hexyn-2-one, 86% ee for 5,5-dimethyl-3-hexyn-2-one, 74% ee for 3-nonyn-2-one and 61% ee for 4-phenyl-3-butyn-2-one. Terminal ${\alpha},{\beta}$-acetylenic ketones, such as 3-butyn-2-one, 1-pentyn-3-one, 4-methyl-1-pentyn-3-one and 1-octyn-3-one, are reduced to the corresponding alcohols with 59% ee, 17% ee, 44% ee and 12% ee of optical induction respectively. With one exception (4-methyl-1-pentyn-3-one), all propargyl alcohols obtained are enriched in R-enantiomers.

• Journal of the Korean Chemical Society
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• v.52 no.4
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• pp.369-379
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• 2008

• Journal of the Korean Chemical Society
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• v.40 no.6
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• pp.415-419
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• 1996

Hydrogen bonding, dielectric effects and steric effects are all factors which determine the carbonyl stretching frequency, νC=O of ketones in solution. The νC=O frequency of ketones is affected by change in concentration of ketones in various solvents. The νC=O frequency shifts to lower frequency in nonpolar solvents and shifts to higher frequency in polar solvents with the increasing volume% of ketones. In acetonitrle, the νC=O frequency shifts to higher frequency as the volume% of ketones is increased except dimethyl ketone. The νC=O frequency shifts to lower frequency as the solvent system becomes increasingly polar or with the increasing extent of intermolecular hydrogen bonding, as in the case of increasing volume% chloroform in $CHCl_3$/$CCl_4$ solvent system.

• Applied Biological Chemistry
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• v.31 no.3
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• pp.292-297
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• 1988

The volatiles of whole and homogenated tomato fruits collected by the headspace trapping method using Tenax GC and the simultaneous steam distillation method were identified by GC and GC-MS. Among over 100 GC peaks, 10 alcohols, 6 aldehydes, 4 ketones, 3 esters, 1 phenol and 1 acid were identified from whole tomato fruits, whereas 12 alcohols, 6 aldehydes, 5 ketones, 5 esters, 2 phenols, 1 hydrocarbon and 1 acid were identified from homogenated tomato fruits. By simultaneous steam distillation-extraction, 19 alcohols, 13 hydrocarbons, 9 esters, 9 ketones, 8 aldehydes, 2 phenols, 2 lactones,2 furans, 1 acids and 2 others were identified among over 300 peaks.

• Archives of Pharmacal Research
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• v.18 no.5
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• pp.369-370
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• 1995

• Bulletin of the Korean Chemical Society
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• v.23 no.7
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• pp.937-938
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• 2002

• Journal of the Korean Chemical Society
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• v.51 no.2
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• pp.115-124
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• 2007

A series of α, β-unsaturated ketones are synthesized by Crossed - Aldol condensation reaction, from ecofriendly 6-methoxy-2-naphthyl ketones and substituted benzaldehydes under solvent free conditions using silica-sulfuric acid as a catalytic reagent. The yields of ketones are more than 90% and the catalyst was reusable for further run. There is no appreciable decrease in the yield of product and the activity of catalyst. These chalcones were characterized by their physical constants and spectral data (IR, 1H-, 13C-NMR and Mass). These spectral data are subjected to correlate various Hammett substituent constants with single and multiparameter correlation equations. From the results of statistical analysis the influence of electronic effects of substituents on the spectral data of the ketones were explained.

• Bulletin of the Korean Chemical Society
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• v.3 no.3
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• pp.119-122
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• 1982

Rigid ${\alpha}$-oximino ketones containing two functional groups such as 2-oximino-1-acenaphthenone and 2-oximino-1-indanone were synthesized and the simultaneous reduction of the two functional groups of ${\alpha}$-oximino ketones by $LiAlH_4$ gave the corresponding amino alcohols, 2-amino-1-acenaphthenol and 2-amino-1-indanol. The yields of the reduction products of the ${\alpha}$ -oximino ketones remarkably increased, as the increase of molar ratio of hydride used to the reactant. The use of 24 moles of $LiAlH_4$ was found to afford the best result in the reduction of the rigid ${\alpha}$-oximino ketones to the corresponding amino alcohols. The yields was not affected by the variation of solvents such as ether, THF and diglyme.

• Bulletin of the Korean Chemical Society
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• v.32 no.1
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• pp.291-295
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• 2011

The catalytic enantioselective conjugate addition reaction of $\alpha$-nitroacetate to $\alpha,\beta$-unsaturated enones promoted by chiral bifunctional organocatalysts is described. The treatment of $\alpha$-nitroacetate to $\alpha,\beta$-unsaturated enones afforded the corresponding Michael adducts with high enantioselectivity. The conjugate addition adducts are easily converted to chiral $\gamma$-nitro ketones and $\delta$-keto esters.