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Pure Appl. Chem., 1988, Vol. 60, No. 1, pp. 79-88

http://dx.doi.org/10.1351/pac198860010079

Stereospecific synthesis of olefins through sequential cross-coupling reactions

F. Naso

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  • Zhao Hong, Yang Weisen, Xie Shiyun, Cai Mingzhong: Stereoselective Synthesis of Difunctionalized 1,3-Dienes Containing Tin and Sulfonyl Groups by Palladium-Catalyzed Regio- and Stereocontrolled Addition Reactions. Eur J Org 2012, 2012, 831. <http://dx.doi.org/10.1002/ejoc.201101153>
  • Cai Mingzhong, Fang Xiaoniu, Dai Ruchun, Zha Lingfang: A one-pot, stereoselective synthesis of 2-ethoxycarbonyl-substituted 1,3-dienes and 1,3-enynes by hydrostannylation-Stille tandem reaction of tributyltin hydride with alkynyl esters and alkenyl or alkynyl halides. Appl Organometal Chem 2009, 23, 229. <http://dx.doi.org/10.1002/aoc.1502>
  • Ye Xinglin, Wang Pingping, Liu Jiaqin, Cai Mingzhong: Stereoselective Synthesis of Difunctionalized 1,3-Dienes Containing Silicon and Selenium via Hydrozirconation of (Z)-3-(Trimethylsilyl)alk-3-en-1-ynes. Synth Comm 2009, 39, 2378. <http://dx.doi.org/10.1080/00397910802654864>
  • Zhao Hong, Dai Ruchun, Cai Mingzhong: Stereoselective Synthesis of (1Z,3E)-2-Ethoxycarbonyl-Substituted 1,3-Dienes via Stille Coupling of (E)-α-Stannyl-α,β-Unsaturated Esters with Alkenyl Halides. Synth Comm 2009, 39, 4454. <http://dx.doi.org/10.1080/00397910902906610>
  • Cai Ming-Zhong, Wang Yue, Wang Ping-Ping: A facile stereoselective synthesis of difunctionalized 1,3-dienes containing tin and halogen via hydrozirconation of (Z)-3-(tributylstannyl)alk-3-en-1-ynes. J Organomet Chem 2008, 693, 2954. <http://dx.doi.org/10.1016/j.jorganchem.2008.06.002>
  • HU Rong-Hua, CHEN Gui-Qin, CAI Ming-Zhong: A Novel Stereoselective Synthesis of (1Z,3E)-2-Phenyl(orp-Tolyl)sulfonyl-substituted 1,3-Dienes via Palladium Catalyzed Cross-coupling Reactions of (E)-α-Iodovinyl Sulfones. Chin J Chem 2007, 25, 1927. <http://dx.doi.org/10.1002/cjoc.200790355>
  • Cai Ming-Zhong, Chen Gui-Qin, Hao Wen-Yan, Wang Dong: A facile stereoselective synthesis of 1,3-dienyl sulfones via Stille coupling reactions of (E)-α-stannylvinyl sulfones with alkenyl iodides. J Organomet Chem 2007, 692, 1125. <http://dx.doi.org/10.1016/j.jorganchem.2006.11.014>
  • Cai Ming-Zhong, Wang Dong, Wang Ping-Ping: Novel stereoselective synthesis of 1-substituted 1,3-dien-2-yl sulfides via Stille coupling reactions of (E)-α-stannylvinyl sulfides with alkenyl iodides. J Organomet Chem 2006, 691, 737. <http://dx.doi.org/10.1016/j.jorganchem.2005.10.012>
  • Luh Tien-Yau, Lee Chin-Fa: Dithioacetals as Zwitterion Synthons. Eur J Org Chem 2005, 2005, 3875. <http://dx.doi.org/10.1002/ejoc.200500245>
  • Cai Mingzhong, Ye Hongde, Zhao Hong, Song Caisheng: Stereoselective synthesis of 1,3-dienylstannanes by palladium catalyzed cross-coupling reactions. J Organomet Chem 2003, 687, 462. <http://dx.doi.org/10.1016/j.jorganchem.2003.09.011>
  • Cai Mingzhong, Hao Wenyan, Zhao Hong, Song Caisheng: Novel stereoselective synthesis of 1,3-dienylsilanes via hydromagnesiation reaction of alkynylsilanes. J Organomet Chem 2003, 679, 14. <http://dx.doi.org/10.1016/S0022-328X(03)00461-3>
  • Cai Ming-Zhong, Huang Jia-Di, Peng Chun-Yun: Stereoselective synthesis of (Z,E)-2-phenylselenobutadienes by palladium-catalyzed cross-coupling reaction. J Organomet Chem 2003, 681, 98. <http://dx.doi.org/10.1016/S0022-328X(03)00583-7>
  • Wang Ya-Pin, Wu Lu-Ling, Huang Xian: A FACILE STEREOSELECTIVE SYNTHESIS OF (E,E)-CONJUGATED DIENYL TELLURIDES BY PALLADIUM-CATALYZED CROSS-COUPLING REACTION. Synth Common 2001, 31, 2803. <http://dx.doi.org/10.1081/SCC-100105329>
  • Benshafrut Ronnie, Rabinovitz Mordecai, Dee-Noor-Barzilay Zohar, de Meijere Armin: Metal reduction of di- and trisubstituted styrylbenzenes: formation of the highly charged tetra- and hexaanions. J Phys Org Chem 1999, 12, 333. <http://dx.doi.org/10.1002/(SICI)1099-1395(199904)12:4<333::AID-POC118>3.0.CO;2-J>
  • Luh Tien-Yau: Chelation Assisted Conversion of C-S Bonds into C-C Bonds. Phosphorus Sulfur Silicon Relat Elem 1997, 120, 259. <http://dx.doi.org/10.1080/10426509708545523>
  • Zhu Liu-Sheng, Huang Zhi-Zhen, Huang Xian: Stereoselective synthesis of (E,E)-1-arylselenobutadienes by cross-coupling reactions in the presence of palladium catalyst. Tetrahedron 1996, 52, 9819. <http://dx.doi.org/10.1016/0040-4020(96)00513-3>
  • Denmark Scott E., Chen Chien-Tien: Enantioselective synthesis of alkylidene cyclohexanes by an asymmetric olefination/cross-coupling sequence. Heteroatom Chem 1995, 6, 133. <http://dx.doi.org/10.1002/hc.520060207>
  • Stadnichuk M D, Voropaeva T I: Silicon-containing alka-1,3-dienes and their functional derivatives in organic synthesis. RUSS CHEM REV 1995, 64, 25. <http://dx.doi.org/10.1070/RC1995v064n01ABEH000135>
  • Babudri Francesco, Fiandanese Vito, Naso Francesco, Punzi Angela: A new straightforward and general approach to dienamide natural products. Tetrahetron Lett 1994, 35, 2067. <http://dx.doi.org/10.1016/S0040-4039(00)73051-6>
  • Babudri Francesco, Fiandanese Vito, Mazzone Luigia, Naso Francesco: A general approach to conjugated (E,E)-dienes through sequential coupling reactions. Tetrahetron Lett 1994, 35, 8847. <http://dx.doi.org/10.1016/S0040-4039(00)78514-5>
  • Fiandanese Vito, Punzi Angela, Ravasio Nicoletta: An easy approach to 1-silylated ketones and asymmetrical 1,6- and 1,8-dicarbonyl compounds. J Organomet Chem 1993, 447, 311. <http://dx.doi.org/10.1016/0022-328X(93)80255-A>
  • Agrios Konstantinos A., Srebnik Morris: Trisubstituted alkenes from alkynes and aryl iodides by boron-to-zinc transmetallation and palladium(0) catalysed cross coupling. J Organomet Chem 1993, 444, 15. <http://dx.doi.org/10.1016/0022-328X(93)83047-Y>
  • Fiandanese Vito, Punzi Angela: A Direct Access to a Potential LTB4-Antagonist, SM-9064, via, Disilyl Derivatives. Synth Common 1993, 23, 173. <http://dx.doi.org/10.1080/00397919308009765>
  • Ager David J., East Michael B.: Methodology to establish 1,2- and 1,3-difunctionality for the synthesis of carbohydrate derivates. Tetrahedron 1992, 48, 2803. <http://dx.doi.org/10.1016/S0040-4020(01)90970-6>
  • Cardellicchio Cosimo, Fiandanese Vito, Naso Francesco, Scilimati Antonio: Optically active sulfoxides by enantiospecific reactions of bromovinyl aryl sulfoxides with grignard reagents. Tetrahetron Lett 1992, 33, 5121. <http://dx.doi.org/10.1016/S0040-4039(00)61207-8>
  • Hegedus Louis S.: Transition metals in organic synthesis annual survey covering the year 1988. J Organomet Chem 1990, 380, 169. <http://dx.doi.org/10.1016/0022-328X(90)80270-A>
  • Howard Black T., Eisenbeis Shane A., McDermott Todd S., Maluleka Stephen L.: Synthesis of cyclic and acyclic βγ-unsaturated car☐ylic acids Via an E1-type ionization/elimination of β-lactones. Tetrahedron 1990, 46, 2307. <http://dx.doi.org/10.1016/S0040-4020(01)82011-1>
  • Fiandanese V., Marchese G., Naso F., Ronzini L., Rotunno D.: An easy route to insect pheromones with a E-Z or Z-E conjugated diene structure. Tetrahetron Lett 1989, 30, 243. <http://dx.doi.org/10.1016/S0040-4039(00)95171-2>
  • Black T. Howard, Maluleka Stephen L.: Isomerically Pure 2,3-Dialkyl 3-Alkenoic Acids via Ionization/Elimination of β-Lactones. Synth Common 1989, 19, 2885. <http://dx.doi.org/10.1080/00397918908052677>
  • Fiandanese V, Marchese G, Naso F: A new ready route to 1,4-ketoaldehydes and 1,4-diketones with application to the synthesis of z-jasmone and dihydrojasmone. Tetrahetron Lett 1988, 29, 3587. <http://dx.doi.org/10.1016/0040-4039(88)85300-0>
  • Fiandanese V., Marchese G., Mascolo G., Naso F., Ronzini L.: Stereospecific synthesis of (1E,3Z)- and (1E,3E)-1-trimethylsilyl-1,3- dienes by means of sequential cross-coupling reactions. Tetrahetron Lett 1988, 29, 3705. <http://dx.doi.org/10.1016/S0040-4039(00)82159-0>