Highly stereoselective synthesis of trisubstituted olefins via addition of alkylcopper complexes to acetylenes

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This article has been cited by 14 ACS Journal articles (5 most recent appear below).

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  Alkyne Elementometalation−Pd-Catalyzed Cross-Coupling. Toward Synthesis of All Conceivable Types of Acyclic Alkenes in High Yields, Efficiently, Selectively, Economically, and Safely: “Green” Way

  Ei-ichi Negishi, Guangwei Wang, Honghua Rao and Zhaoqing Xu
  The Journal of Organic Chemistry2010 75 (10), 3151-3182

  • Alkyne Elementometalation−Pd-Catalyzed Cross-Coupling. Toward Synthesis of All Conceivable Types of Acyclic Alkenes in High Yields, Efficiently, Selectively, Economically, and Safely: “Green” Way

    Ei-ichi Negishi, Guangwei Wang, Honghua Rao and Zhaoqing Xu
    The Journal of Organic Chemistry2010 75 (10), 3151-3182

    Palladium-catalyzed cross-coupling reactions, especially those involving Zn, Al, Zr (Negishi coupling), and B (Suzuki coupling), collectively have brought about “revolutionary” changes in organic synthesis. Thus, two regio- and stereodefined carbon groups ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Titanocene(III) Chloride Mediated Radical-Induced Addition to Baylis−Hillman Adducts: Synthesis of (E)- and (Z)-Trisubstituted Alkenes and α-Methylene/Arylidene δ-Lactones

  Samir K. Mandal, Moumita Paira and Subhas C. Roy
  The Journal of Organic Chemistry2008 73 (10), 3823-3827

  • Titanocene(III) Chloride Mediated Radical-Induced Addition to Baylis−Hillman Adducts: Synthesis of (E)- and (Z)-Trisubstituted Alkenes and α-Methylene/Arylidene δ-Lactones

    Samir K. Mandal, Moumita Paira and Subhas C. Roy
    The Journal of Organic Chemistry2008 73 (10), 3823-3827

    Baylis−Hillman adduct underwent smooth radical-induced condensation with activated bromo compounds and epoxides using titanocene(III) chloride (Cp2TiCl) as the radical generator. The reactions of activated bromo compounds with 3-acetoxy-2-methylene ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Stereoselective Synthesis of Trisubstituted E-Iodoalkenes by Indium-Catalyzed syn-Addition of 1,3-Dicarbonyl Compounds to 1-Iodoalkynes

  Hayato Tsuji, Taisuke Fujimoto, Kohei Endo, Masaharu Nakamura, and Eiichi Nakamura
  Organic Letters2008 10 (6), 1219-1221

  • Stereoselective Synthesis of Trisubstituted E-Iodoalkenes by Indium-Catalyzed syn-Addition of 1,3-Dicarbonyl Compounds to 1-Iodoalkynes

    Hayato Tsuji, Taisuke Fujimoto, Kohei Endo, Masaharu Nakamura, and Eiichi Nakamura
    Organic Letters2008 10 (6), 1219-1221

    Indium-catalyzed addition of 1,3-dicarbonyl compounds to 1-iodo-1-alkynes takes place exclusively in a syn-fashion to produce E-iodoalkenes. The iodine atom serves both as an activating group and as a group that controls the regioselectivity of the ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Tandem Carbocupration/Oxygenation of Terminal Alkynes

  Donghui Zhang and Joseph M. Ready
  Organic Letters2005 7 (25), 5681-5683

  • Tandem Carbocupration/Oxygenation of Terminal Alkynes

    Donghui Zhang and Joseph M. Ready
    Organic Letters2005 7 (25), 5681-5683

    A direct and general synthesis of α-branched aldehydes and their enol derivatives is described. Carbocupration of terminal alkynes and subsequent oxygenation with lithium tert-butyl peroxide generates a metallo-enolate. Trapping with various electrophiles ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Total Syntheses of Epothilones B and D

  Jae-Chul Jung, Rajashaker Kache, Kimberly K. Vines, Yan-Song Zheng, Panicker Bijoy, Muralikrishna Valluri, and Mitchell A. Avery
  The Journal of Organic Chemistry2004 69 (26), 9269-9284

  • Total Syntheses of Epothilones B and D

    Jae-Chul Jung, Rajashaker Kache, Kimberly K. Vines, Yan-Song Zheng, Panicker Bijoy, Muralikrishna Valluri, and Mitchell A. Avery
    The Journal of Organic Chemistry2004 69 (26), 9269-9284

    A convergent, total synthesis of epothilones B (2) and D (4) is described. The key steps are Normant coupling to establish the desired (Z)-stereochemistry at C12−C13, Wadsworth−Emmons olefination of methyl ketone 28 with the phosphonate ester 8, ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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