• Title/Summary/Keyword: Wittig Reaction

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Facile Synthesis of Aldehyde-focal Fréchet Type Dendrons and Dendrimers via Staudinger/Aza-Wittig Reactions

  • Han, Seung-Choul;Jin, Sung-Ho;Lee, Jae-Wook
    • Bulletin of the Korean Chemical Society
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    • v.32 no.10
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    • pp.3624-3628
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    • 2011
  • Fr$\acute{e}$chet-type dendritic benzaldehydes were efficiently synthesized using 3,5-dihydroxybenzaldehyde as an aldehyde focal point functionalized unit by adding a generation to the existing dendron or direct oxidation of Fr$\acute{e}$chet-type dendritic benzyl alcohols. These dendritic benzaldehydes were applied for the construction of dendrimers containing secondary amines as connectors via Staudinger/aza-Wittig Reactions with ${\alpha}$,${\alpha}'$,-diazidop-xylene core.

An Efficient Synthesis of 12-epi-Carbacyclins Using a Palladium-Mediated Tandem Alkene Insertion Strategy

  • Lee, Nam-Ho;Larock, Richard C.
    • Bulletin of the Korean Chemical Society
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    • v.23 no.1
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    • pp.86-92
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    • 2002
  • A short synthesis of novel prostanoids, 12-epi-carbacyclins 3 and 24, has been accomplished using palladium chemistry as a key step. The silyl enol ether 10a prepared through organopalladium chemistry has been allowed to react with 1-octen-3-one in the presence of $Pd(OAc)_2$ to give compound 12 in a single step. The unusual chemo- and stereoselective reduction of the ${\alpha},{\beta}$-unsaturated ketone in 12 has been effected with (S)-BINALH. Subsequent desilylation and Wittig reaction have provided the Subsequent desilylation and Wittig reaction have provided the $PGI_2$ analogues 3 and 24.

Preparation of Fully Substituted 1,3,4-Oxadiazole Derivatives from N-Isocyaniminotriphenylphosphorane, (E)-Cinnamic Acids, Chloroacetone and Primary Amines

  • Ramazani, Ali;Nasrabadi, Fatemeh Zeinali;Karimi, Zahra;Rouhani, Morteza
    • Bulletin of the Korean Chemical Society
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    • v.32 no.8
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    • pp.2700-2704
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    • 2011
  • The 1:1 imine intermediate generated by the addition of primary amine to chloroacetone is trapped by N-isocyaniminotriphenylphosphorane in the presence of (E)-cinnamic acids and the corresponding iminophosphorane intermediate was formed. Disubstituted 1,3,4-oxadiazole derivatives are formed via intramolecular aza-Wittig reaction of the iminophosphorane intermediate. The reactions were completed in neutral conditions at room temperature. The disubstituted 1,3,4-oxadiazole derivatives were produced in excellent yields.

Synthesis of (Z)-, and (E)-8-Dodecen-1-yl Acetate, The Sex Pheromone of the Oriental Fruit Moth, Grapholitha Molesta by Stereochemical Control in Wittig Olefination

  • Kang, Suk-Ku;Kim, Jung-Hawn;Shin, Yaung-Chul
    • Bulletin of the Korean Chemical Society
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    • v.7 no.6
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    • pp.453-457
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    • 1986
  • Stereochemical control of the Wittig reaction of the primary aldehyde, 8-acetoxyoctan-1-al (7) with the nonstabilized alkylide, triphenylphosphonium n-butylide (6), was achieved by controlling the reaction conditions including solvent, temperature and inorganic salts. These conditions can be applied to the direct sythesis of the mixture of (Z)-, and (E)-8-dodecen-1-yl acetate, the sex pheromone of the oriental fruit moth, Grapholitha molesta. The primary aldehyde, 8-acetoxyoctan-1-al (7) was synthesized from 1,8-octanediol which is cheap and readily available.

Facial Synthesis of Versatile Chiral Norbornenes as Leukotriene D4 Antagonists from D-glucose

  • Lim, Yoong-Ho;Koh, Dong-Soo
    • Journal of Applied Biological Chemistry
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    • v.48 no.2
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    • pp.97-100
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    • 2005
  • Chiral dienophile 5 was synthesized from D-glucose by consecutive diisopropylidenation, partial deprotection, diol cleavage, and Wittig reactions. Under thermal conditions, asymmetric Diels-Alder reaction between chiral dienophile and cyclopentadiene gave four possible chiral norbornenes stereoisomers whose absolute configurations were determined through CADD and NMR.

A Straightforward Synthesis of K-7174, a GATA-Specific Inhibitor

  • Majik, Mahesh S.;Yu, Jin-Ha;Jeong, Lak-Shin
    • Bulletin of the Korean Chemical Society
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    • v.33 no.9
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    • pp.2903-2906
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    • 2012
  • K-7174, a GATA-specific inhibitor, is a putative anti-inflammatory agent that attenuates effects of inflammatory cytokines in certain cell types. An expeditious four-step synthesis of K-7174 is described in this paper. The route employs Wittig olefination and bis-alkylation of homopiperazine as the key reactions. The iodine-catalyzed isomerization of the Z-isomer results in complete conversion to the E-isomer is the highlight of our synthetic endeavors.

Synthesis and Luminescent Properties of Blue Light Emitting Polymers Containing a 4,4' or 3,3'-Linked Biphenyl Unit

  • Ahn, Taek
    • Transactions on Electrical and Electronic Materials
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    • v.13 no.6
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    • pp.317-321
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    • 2012
  • Poly[4,4'(3,3')-biphenylenevinylene-alt-2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylene-vinylene], 4,4'(3,3')-PBPMEH-PPV, and poly[4,4'(3,3')-biphenylenevinylene-alt-N-ethylhexyl-3,6-carbazolevinylene], 4,4'(3,3')-PBPCAR-PPV, of varying effective conjugation lengths, were synthesized by the well-known Wittig condensation polymerization between the appropriate biphenyl diphosphonium salts and dialdehyde monomers such as carbazole or dialkoxyphenyl dialdehyde. The conjugation lengths of the polymers were controlled by biphenyl linkages (4,4' or 3,3'). The resulting polymers were highly soluble in common organic solvents and exhibited good thermal stability up to $300^{\circ}C$. The synthesized polymers showed UV-visible absorbance and photoluminescence (PL) in the ranges of 314-400 nm and 430-507 nm, respectively. Carbazole and 3,3'-biphenyl containing 3,3'-PBPCAR-PPV showed a blue PL peak at 430 nm. A single-layer light-emitting diode was fabricated in a configuration of ITO/polymer/Al. Electroluminescence (EL) emission of 3,3'-PBPCAR-PPV was shown at 455 nm.