• Bulletin of the Korean Chemical Society
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• 제23권10호
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• pp.1375-1376
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• 2002

• Bulletin of the Korean Chemical Society
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• 제30권11호
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• pp.2519-2520
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• 2009

• Bulletin of the Korean Chemical Society
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• 제22권9호
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• pp.958-962
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• 2001

The chiral amine auxiliary mediated stereoselective alkylation reactions of glycinamides 1-6 and 15-17 using phase transfer catalyst (PTC) for liquid-solid extraction are described. The secondary N-(diphenylmethylene) glycinamides 1, 2 and 3 give better selectivities and yields than tertiary N-(diphenylmethylene) glycinamides 4, 5 and 6. Alkylation of the glycinamide 1 and 2 using 18-Crown-6 as a PTC in toluene at $-40^{\circ}C$ gives best selectivities and yields. Alkylations of N-(4-chlorophenylmethylene)glycinamides 15, 16 and 17 under same PTC conditions give $\alpha$, $\alpha-disubstituted$ amino acid derivatives 18, 19 and 20 with low diastereoselectivities.

• Bulletin of the Korean Chemical Society
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• 제33권5호
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• pp.1617-1621
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• 2012

The titanate nanotube (TNT) was hydrothermally synthesized in 10 M NaOH aqueous solution at $150^{\circ}C$ for 72 h. Titanate nanotube with high surface area (292 $m^2$/g) is a good candidate as a support for catalytic reaction or organic synthesis. Palladium nanoparticles with an average size of $ca$. 3 nm were well dispersed onto the surface of TNT nanotubes. Palladium loaded catalyst with high surface area shows a highly efficient ${\alpha}$ alkylation of ketones with primary alcohols.

• Archives of Pharmacal Research
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• 제19권2호
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• pp.148-152
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• 1996

The efficient synthesis of 4-(2-thiazolyloxy)phenylalkanoic acids (10a-c), which are a potent antiinflammatory agent, was achieved in 5-6 steps starting from isopropoxybenzene and methyl $\alpha-chloro-\alpha-(methylthio)acetate (1)$. The key intermediate (4) was prepared by Friedel-Crafts reaction of isopropoxybenzene with (1) followed by desulfurization and the removal of isopropyl protector. Methyl 4-hydroxyphenylalkanoates (6, 8) were similarly obtained from alkylation of (3) and deprotection.

• 대한약학회:학술대회논문집
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• 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.1
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• pp.244.2-244.2
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• 2003

For the development of new synthetic method for unnatural amino acid esters, alkyl ${\alpha}$-anilinophenylacetates were synthesized through base-catalyzed hydrolysis of 1,5-diphenylhydantoins in methanol and O-alkylation of sodium ${\alpha}$-anilinophenylacetate with alkyl halides in DMF. Even though hydrolysis of hydantoin ring was undertaken under about 30-40$^{\circ}C$ in methanol, the hydantoic acid sodium salt was continuously converted to the sodium ${\alpha}$-anilinophenylacetate. (omitted)

• Archives of Pharmacal Research
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• 제28권2호
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• pp.129-141
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• 2005

(-)-Fumagillol (1), a hydrolysis product of fumagillin, has been synthesized by several group from commercially available 1,2:5,6-di-O-isopropylidene-${\alpha}$-D-allofuranose in a highly stereoselective manner. Chiral centers on C5 and C6 came from D-allofuranose and the asymmetric center on C4 was accomplished by 1,3-chirality transfer using the Claisen rearrangement on a chiral allyl alcohol. Chirality, which is necessary on an epoxide consisting of the spiro-ring system, was diastereoselectively constructed by the well-known reaction, intramolecular ester enolate alkylation (IEEA), which showed that this reaction can be applied to the alpha-alkoxy ester system. The epoxide on the side chain was regioselectively introduced by the difference between the number of substituents on the vinyl groups. This accomplishment proved that IEEA can be a useful tool for the synthesis of complex molecules.

• Bulletin of the Korean Chemical Society
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• 제21권8호
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• pp.767-768
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• 2000

• Bulletin of the Korean Chemical Society
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• 제23권5호
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• pp.769-772
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• 2002

• Bulletin of the Korean Chemical Society
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• 제34권10호
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• pp.2953-2958
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• 2013

A noble phenylsulfonyl reagent 8 having ${\alpha}$-oxo (cyanomethylene)triphenylphosphorane ylide subunit readily condensed with various alkyl halides under basic conditions to afford ${\beta}$-alkyl-${\alpha}$-oxo-${\beta}$-phenylsulfonyl (cyanomethylene)triphenylphosphorane ylides 9 in excellent yields. These sulfonyl ylides 9 were then reductively desulfonylated with $Na(Hg)/Na_2HPO_4$ in the presence of methanol to provide ${\alpha}$-keto (cyanomethylene)-triphenylphosphorane ylides 2' in good to excellent yields. Our new synthetic approach offers an expeditious access to various ${\alpha}$-keto (cyanomethylene)triphenylphosphorane ylides from alkyl halides utilizing a new phenylsulfonyl reagent as the key reagent under mild reaction conditions in good overall yields.