• Title/Summary/Keyword: Asymmetric reaction

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Asymmetric Synthesis of 12-epi-$PGF_{2α}$ by a Palladium-Mediated, Three-Component Coupling Reaction

  • 이남호;Richard C. Larock
    • Bulletin of the Korean Chemical Society
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    • v.16 no.9
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    • pp.859-863
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    • 1995
  • The prostaglandin analogue 12-epi-PGF2α (2) has been synthesized from optically active cis-4-t-butyldimethylsilyloxy-2-cyclopenten-1-ol (4b) in 4 steps in an overall yield of 21%. An extremely efficient Pd(Ⅱ)-mediated, three-component coupling reaction is employed to obtain the key intermediate 9.

Asymmetric Hydrogenation of Ethyl Pyruvate over Bimetallic Rh-Pt/Al2O3 Catalysts Modified with Dihydrocinchonidine (Dihydrocinchonidine으로 개질된 Rh-Pt/Al2O3 이원금속 촉매를 이용한 Ethyl Pyruvate의 비대칭 수소화)

  • Cho, Hong-Baek;Kang, Joon-seok;Park, Yeung-Ho
    • Applied Chemistry for Engineering
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    • v.17 no.4
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    • pp.369-374
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    • 2006
  • $Rh-Pt/Al_{2}O_{3}$ catalysts were used for the first time to study its reaction characteristics in the asymmetric hydrogenation of ethyl pyruvate. The catalysts were prepared either by impregnation of Rh on a commercial $Pt/Al_{2}O_{3}$ or by sequential impregnation of Rh followed by impregnation of Pt on $Al_{2}O_{3}$. Reaction rate and enantiomeric excess (ee%) were compared according to the preparation method, Rh contents, and the reduction temperature of the catalyst. The physical characteristics of the catalysts were analyzed using XRD and TEM. Bimetallic $Rh-Pt/Al_{2}O_{3}$ catalysts showed an improved reaction rate and optical purity (63.6 ee%) with increasing the reduction temperature. The variation of the Rh contents as well as the preparation method elicited a big difference on the reaction rate, while enantiomeric excess (ee%) was lower (56~60%) with all bimetallic catalysts than with monometallic $Pt/Al_{2}O_{3}$ catalyst.

Biomimetic Catalysis in Ionic Liquids: Markedly Enhanced Enantioselectivity in Amino Acid-Catalyzed Directed Asymmetric Aldol Reactions

  • Yun, Suk-Jin;Lee, Jae Kwan
    • Journal of Integrative Natural Science
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    • v.8 no.2
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    • pp.107-110
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    • 2015
  • Amino acid-catalyzed directed asymmetric aldol reactions showed enhanced enantioselectivity when conducted in ionic liquids. Optically active products were afforded in better yields (up to 23% higher) and enantiomeric excess (up to 21% higher) in ionic liquids than in conventional organic solvents.

Organocatalytic Asymmetric Michael Addition of 1,3-Cyclohexanedione to Benzylidenemalonitriles

  • Suh, Chang Won;Kim, Dae Young
    • Bulletin of the Korean Chemical Society
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    • v.35 no.1
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    • pp.98-102
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    • 2014
  • The organocatalytic enantioselective Michael addition reaction promoted by chiral binaphthyl-modified squaramide catalyst have been developed, allowing facile synthesis of the corresponding chiral 2-amino-4H-chromenes derivatives with excellent enantioselectivity (up to 99% ee). The method reported represents a practical entry for the preparation of chiral 2-amino-4H-chromenes derivatives.

Synthesis and Characterization of New Push-Pull Chromophores Containing BF2-Azopyrrole Derivatives

  • Ko, HayeMin
    • Journal of the Korean Chemical Society
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    • v.60 no.1
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    • pp.21-27
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    • 2016
  • Novel push-pull chromophores containing 5’-(4-(bis(9,9-dimethyl-9H-fluoren-2-yl)aniline (bisDMFA) as a donor and phenylazo-methylpyrrolyl-boron difluoride (PhAPy-BF2) as an acceptor were designed and synthesized by the Knoevenagel condensation reaction for organic solar cells. Various electron withdrawing moieties were effectively introduced using 2,4-dimethyl-1H-pyrrole to afford new asymmetric BF2-azopyrrole molecules that were characterized by UV-vis spectroscopy and cyclic voltammetry measurements.

A novel bromolactonization reaction using racemic 2-bromo-5-isobutyl-5-methylhydantoin

  • Cho, Youn-Sang;Jew, Sang-Sup;Chung, You-sup
    • Archives of Pharmacal Research
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    • v.5 no.2
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    • pp.93-96
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    • 1982
  • By using recemic 3-bromo-5-isobutyl-5-methylhydantoin (3a') in dry N, N-dimethylformamide which is a model reagent for asymmetric bromolactonization, bromolactonization of a series of olefinic acids was carried out to furnish corresponding bromolactones in moderate yields.

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A Stereoselective Asymmetric Synthesis of Antibiotic (-)-Fumagillol Using Claisen Rearrangement and Intramolecular Ester Enolate Alkylation as Key Steps

  • Kim Deukjoon;Ahn Soon Kil;Bae Hoon;Kim Hak Sung
    • Archives of Pharmacal Research
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    • v.28 no.2
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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.