CrossRef enabled

PAC Archives

Archive →

Pure Appl. Chem., 1992, Vol. 64, No. 3, pp. 323-334

http://dx.doi.org/10.1351/pac199264030323

Zipper-mode cascade carbometallation for construction of polycyclic structures

E. Negishi

CrossRef Cited-by theme picture

CrossRef Cited-by Linking

  • Lechel Tilman, Pfrengle Fabian, Reissig Hans-Ulrich, Zimmer Reinhold: Three Carbons for Complexity! Recent Developments of Palladium-Catalyzed Reactions of Allenes. ChemCatChem 2013, 5, 2100. <http://dx.doi.org/10.1002/cctc.201200875>
  • Muzart Jacques: Three to seven C–C or C–heteroatom bonds from domino reactions involving a Heck process. Tetrahedron 2013, 69, 6735. <http://dx.doi.org/10.1016/j.tet.2013.05.061>
  • Barluenga José, Sigüeiro Rita, Vicente Rubén, Ballesteros Alfredo, Tomás Miguel, Rodríguez Miguel A.: Gold-Catalyzed Functionalization of Unactivated C(sp3 )H Bonds by Hydride Transfer Facilitated by Alkynylspirocyclopropanes. Angew. Chem. 2012, 124, 10523. <http://dx.doi.org/10.1002/ange.201205051>
  • Barluenga José, Sigüeiro Rita, Vicente Rubén, Ballesteros Alfredo, Tomás Miguel, Rodríguez Miguel A.: Gold-Catalyzed Functionalization of Unactivated C(sp3 )H Bonds by Hydride Transfer Facilitated by Alkynylspirocyclopropanes. Angew. Chem. Int. Ed. 2012, 51, 10377. <http://dx.doi.org/10.1002/anie.201205051>
  • Vlaar Tjøstil, Ruijter Eelco, Orru Romano V. A.: Recent Advances in Palladium-Catalyzed Cascade Cyclizations. Synth Catal 2011, 353, 809. <http://dx.doi.org/10.1002/adsc.201000979>
  • NEGISHI E.: ChemInform Abstract: Zipper-Mode Cascade Carbometallation for Construction of Polycyclic Structures. ChemInform 2010, 23, no. <http://dx.doi.org/10.1002/chin.199232277>
  • Lutz Vanessa, Baro Angelika, Fischer Peter, Laschat Sabine: Synthesis of Functionalized Hydropentalenes by an Asymmetric Deprotonation/Alkylation Strategy. Eur J Org 2010, 2010, 1149. <http://dx.doi.org/10.1002/ejoc.200901154>
  • Dzhemilev Usein M., Ibragimov Askhat G.: Catalytic cyclometalation reaction of unsaturated compounds in synthesis of magnesa- and aluminacarbocycles. J Organomet Chem 2010, 695, 1085. <http://dx.doi.org/10.1016/j.jorganchem.2010.01.002>
  • Huang Xian, Zhu Shugao, Shen Ruwei: Palladium-Catalyzed Sequential Reactions via Allene Intermediates for the Rapid Synthesis of Fused Polycyclic Pyrrole Derivatives. Adv Synth Catal 2009, 351, 3118. <http://dx.doi.org/10.1002/adsc.200900503>
  • Shen Ruwei, Chen Linzhu, Huang Xian: Facile Synthesis of Polycyclic Fluorene Derivatives via a Palladium-Catalyzed Coupling, Propargyl-Allenyl Isomerization and Schmittel Cyclization Sequence. Adv Synth Catal 2009, 351, 2833. <http://dx.doi.org/10.1002/adsc.200900600>
  • Shen Ruwei, Huang Xian, Chen Lingzhu: A Facile and Efficient Synthesis of Dihydroisobenzofuran Derivatives via Tandem Palladium-Catalyzed Coupling, Propargyl-Allenyl Rearrangement, [4+2] Cycloaddition and Aromatization Reaction. Adv Synth Catal 2008, 350, 2865. <http://dx.doi.org/10.1002/adsc.200800470>
  • Chen Mao, Weng Yue, Guo Mian, Zhang Hua, Lei Aiwen: Nickel-Catalyzed Reductive Cyclization of Unactivated 1,6-Enynes in the Presence of Organozinc Reagents. Angew Chem 2008, 120, 2311. <http://dx.doi.org/10.1002/ange.200704452>
  • Chen Mao, Weng Yue, Guo Mian, Zhang Hua, Lei Aiwen: Nickel-Catalyzed Reductive Cyclization of Unactivated 1,6-Enynes in the Presence of Organozinc Reagents. Angew Chem Int Ed 2008, 47, 2279. <http://dx.doi.org/10.1002/anie.200704452>
  • Sünnemann Hans Wolf, Banwell Martin G., de Meijere Armin: Diversity-Oriented Synthesis of Enantiomerically Pure Steroidal Tetracycles Employing Stille/Diels-Alder Reaction Sequences. Chem Eur J 2008, 14, 7236. <http://dx.doi.org/10.1002/chem.200800601>
  • Pinto Artur, Jia Yanxing, Neuville Luc, Zhu Jieping: Palladium-Catalyzed Enantioselective Domino Heck–Cyanation Sequence: Development and Application to the Total Synthesis of Esermethole and Physostigmine. Chem Eur J 2007, 13, 961. <http://dx.doi.org/10.1002/chem.200601016>
  • Sünnemann Hans Wolf, Hofmeister Anja, Magull Jörg, de Meijere Armin: Stille–Heck Coupling Sequences Applied in a Versatile New Access to Steroid Skeletons. Chem Eur J 2007, 13, 3739. <http://dx.doi.org/10.1002/chem.200601240>
  • Szlosek-Pinaud Magali, Diaz Philippe, Martinez Jean, Lamaty Frédéric: Efficient synthetic approach to heterocycles possessing the 3,3-disubstituted-2,3-dihydrobenzofuran skeleton via diverse palladium-catalyzed tandem reactions. Tetrahedron 2007, 63, 3340. <http://dx.doi.org/10.1016/j.tet.2007.02.035>
  • Khafizova L. O., Gilyazev R. R., Tyumkina T. V., Ibragimov A. G., Dzhemilev U. M.: Cycloalumination of α,ω-diolefins with EtAlCl2 catalyzed by zirconium complexes. Russ J Org Chem 2007, 43, 961. <http://dx.doi.org/10.1134/S1070428007070032>
  • Becheanu Armand, Baro Angelika, Laschat Sabine, Frey Wolfgang: Synthesis of Highly Functionalized Pentalenes via IntermolecularPauson–Khand Reaction. Eur J Org Chem 2006, 2006, 2215. <http://dx.doi.org/10.1002/ejoc.200500966>
  • Ramón Diego J., Yus Miguel: Neue Entwicklungen in der asymmetrischen Mehrkomponenten-Reaktion. Angew Chem 2005, 117, 1628. <http://dx.doi.org/10.1002/ange.200460548>
  • Ramón Diego J., Yus Miguel: Asymmetric Multicomponent Reactions (AMCRs): The New Frontier. Angew Chem Int Ed 2005, 44, 1602. <http://dx.doi.org/10.1002/anie.200460548>
  • Bräse Stefan, Wertal (nee Nüske) Hanno, Frank Daniel, Vidović Denis, de Meijere Armin: Intramolecular Heck Couplings and Cycloisomerizations of Bromodienes and Enynes with 1′,1′-Disubstituted Methylenecyclopropane Terminators: Efficient Syntheses of [3]Dendralenes. Eur J Org Chem 2005, 2005, 4167. <http://dx.doi.org/10.1002/ejoc.200500330>
  • Zhang Daohua, Yum Eul Kgun, Liu Zhijian, Larock Richard C.: Synthesis of Indenes by the Palladium-Catalyzed Carboannulation of Internal Alkynes. Org Lett 2005, 7, 4963. <http://dx.doi.org/10.1021/ol051907a>
  • Bruyère Didier, Bouyssi Didier, Balme Geneviève: A study on the regio- and stereoselectivity in palladium-catalyzed cyclizations of alkenes and alkynes bearing bromoaryl and nucleophilic groups. Tetrahedron 2004, 60, 4007. <http://dx.doi.org/10.1016/j.tet.2004.03.023>
  • Szlosek-Pinaud Magali, Diaz Philippe, Martinez Jean, Lamaty Frédéric: Palladium-catalyzed cascade allylation/carbopalladation/cross coupling: a novel three-component reaction for the synthesis of 3,3-disubstituted-2,3-dihydrobenzofurans. Tetrahetron Lett 2003, 44, 8657. <http://dx.doi.org/10.1016/j.tetlet.2003.09.169>
  • Chandrasekhar S., Narsihmulu Ch., Reddy N.Ramakrishna, Reddy M.Srinivasa: Triethylborane triggered intermolecular domino Michael–aldol three-component coupling reactions. Tetrahetron Lett 2003, 44, 2583. <http://dx.doi.org/10.1016/S0040-4039(03)00246-6>
  • Sauvagnat Bérengère, Lamaty Frédéric, Lazaro René, Martinez Jean: Highly selective intermolecular Heck reaction for the soluble polymer supported synthesis of glutamic acid analogues. Tetrahedron 2001, 57, 9711. <http://dx.doi.org/10.1016/S0040-4020(01)00984-X>
  • Catellani Marta, Cugini Federica, Tiefenthaler Domenico: New pathways of site selective aromatic alkylation of palladium complexes: fragmentation to arenes vs. ring closure to hexahydromethano-fluorenes or -phenanthrenes. Can J Chem 2001, 79, 742. <http://dx.doi.org/10.1139/v01-047>
  • Chakraborty Arindam, Marek Ilan: New One-Pot Synthesis of ò-Iodoalkyne. Synthetic Communications 2000, 30, 1895. <http://dx.doi.org/10.1080/00397910008087238>
  • Ibragimov A. G., Khafizova L. O., Satenov K. G., Khalilov L. M., Yakovleva L. G., Rusakov S. V., Dzhemilev U. M.: Synthesis and transformations of metallacycles. Russ Chem Bull 1999, 48, 1574. <http://dx.doi.org/10.1007/BF02496415>
  • de Meijere Armin, Bräse Stefan: Palladium in action: domino coupling and allylic substitution reactions for the efficient construction of complex organic molecules. J Organomet Chem 1999, 576, 88. <http://dx.doi.org/10.1016/S0022-328X(98)01087-0>
  • Negishi Ei-ichi, Liou Show-Yee, Xu Caiding, Shimoyama Izumi, Makabe Hidefumi: Intermolecular trapping of acylpalladium and related acylmetal derivatives with active C–H compounds. Journal of Molecular Catalysis A 1999, 143, 279. <http://dx.doi.org/10.1016/S1381-1169(98)00395-1>
  • Dzhemilev U. M., Ibragimov A. G.: A novel reaction of cycloalumination of olefins and acetylenes mediated by metallocomplex catalysts. Russ Chem Bull 1998, 47, 786. <http://dx.doi.org/10.1007/BF02498144>
  • Bocelli Gabriele, Catellani Marta, Chiusoli Gian Paolo, Cugini Federica, Lasagni Barbara, Mad Matteo Neri: Palladium-catalyzed seven-membered N,O-heterocycle ring formation. Inorg Chim Ada 1998, 270, 123. <http://dx.doi.org/10.1016/S0020-1693(97)05832-5>
  • Jankowski Paweł, Marczak Stanisław, Wicha Jerzy: Methods for the construction of trans-hydrindane rings and their origins in steroid chemistry. Vitamin D total synthesis. Tetrahedron 1998, 54, 12071. <http://dx.doi.org/10.1016/S0040-4020(98)00570-5>
  • Catellani Marta, Frignani Franco, Rangoni Armando: Regioselektive Syntheseo,o′-disubstituierter Vinylarene über einen komplexen Katalysecyclus. Angew Chem 1997, 109, 142. <http://dx.doi.org/10.1002/ange.19971090146>
  • Dzhemilev U. M., Ibragimov A. G., Ramazanov I. R., Khalilov L. M.: Aluminacyclopropenes, a novel series of organoaluminum compounds. Russ Chem Bull 1997, 46, 2150. <http://dx.doi.org/10.1007/BF02495275>
  • Copéret Christophe, Ma Shengming, Negishi Ei-Ichi: Palladiumkatalysierte Kaskadencyclisierung von Ioddienen und -trienen unter Carbonylierung. Angew Chem 1996, 108, 2255. <http://dx.doi.org/10.1002/ange.19961081818>
  • Zhu Guoxin, Lu Xiyan: Molecular oxygen promoted oxidative cleavage of carbon-palladium bonds — catalytic cyclization of allylic 2-alkynoates to α-alkylidine-γ-butyrolactones by a PdII complex. J Organomet Chem 1996, 508, 83. <http://dx.doi.org/10.1016/0022-328X(95)05781-J>
  • Copéret Christophe, Ma Shengming, Sugihara Takumichi, Negishi Ei-ichi: Cyclic carbopalladation of alkynes terminated by carbonylative amidation. Tetrahedron 1996, 52, 11529. <http://dx.doi.org/10.1016/0040-4020(96)00640-0>
  • Jiang Huanfeng, Ma Shengming, Zhu Guoxin, Lu Xiyan: Structural factors affecting the selectivities in the palladium (II) catalyzed cyclization of N-alkenyl-2-alkynamides. Tetrahedron 1996, 52, 10945. <http://dx.doi.org/10.1016/0040-4020(96)00648-5>
  • Catellani Marta, Chiusoli Gian Paolo, Marzolini Giovanna, Rossi Emanuela: Designing a catalytic synthesis of 4-methylcoumarin from ortho-iodophenyl 3-butenoate: Ring closure and isomerization control. J Organomet Chem 1996, 525, 65. <http://dx.doi.org/10.1016/S0022-328X(96)06489-3>
  • Catellani Marta, Chiusoli Gian Paolo, Costa Mirco: Transition metal-catalysed organic reactions promoted by chelating or metallacycle-forming substrates. J Organomet Chem 1995, 500, 69. <http://dx.doi.org/10.1016/0022-328X(95)00526-V>
  • Dzhemilev U.M: New achievements in the use of zirconium complexes in the chemistry of organo-aluminium and magnesium compounds. Tetrahedron 1995, 51, 4333. <http://dx.doi.org/10.1016/0040-4020(94)01123-H>
  • Nylund Christine S., Smith Daniel T., Klopp John M., Weinreb Steven M.: A palladium-mediated tandem carbon-carbon bond forming method featuring nucleophilic substitution of intermediate π-allylpalladium complexes produced via the heck reaction. Tetrahedron 1995, 51, 9301. <http://dx.doi.org/10.1016/0040-4020(95)00518-D>
  • Copéret Christophe, Sugihara Takumichi, Negishi Ei-ichi: Termination of carbopalladation of alkynes via carbonylative amidation producing lactams. Tetrahetron Lett 1995, 36, 1771. <http://dx.doi.org/10.1016/0040-4039(95)00120-2>
  • Sugihara Takumichi, Takebayashi Masahiro, Kaneko Chikara: Effects of high pressure on the heck reaction. Is it possible to control dehydropalladation of alkylpalladium intermediates having β-hydrogens?. Tetrahetron Lett 1995, 36, 5547. <http://dx.doi.org/10.1016/0040-4039(95)01048-M>
  • Jahn Ullrich, Curran Dennis P.: Towards a tandem-radical macrocyclization-transannular cyclization approach to steroids: Transannular cyclizations of a macrocyclic core. Tetrahetron Lett 1995, 36, 8921. <http://dx.doi.org/10.1016/0040-4039(95)01918-8>
  • Beller Matthias, Cornils Boy, Frohning Carl D., Kohlpaintner Christian W.: Progress in hydroformylation and carbonylation. Journal of Molecular Catalysis A 1995, 104, 17. <http://dx.doi.org/10.1016/1381-1169(95)00130-1>
  • De Meijere Armin, Meyer Frank E.: Kleider machen Leute: Heck-Reaktion im neuen Gewand. Angew Chem 1994, 106, 2473. <http://dx.doi.org/10.1002/ange.19941062307>
  • Balme Geneviève, Bouyssi Didier: Total synthesis of the triquinane marine sesquiterpene (±)Δ9(12) capnellene using a palladium-catalyzed bis-cyclization step. Tetrahedron 1994, 50, 403. <http://dx.doi.org/10.1016/S0040-4020(01)80763-8>
  • Grigg Ronald, Redpath James, Sridharan Visuvanathar, Wilson David: Three component palladium catalysed cyclisation-carbonylation-anion capture processes. Tetrahetron Lett 1994, 35, 4429. <http://dx.doi.org/10.1016/S0040-4039(00)73376-4>
  • Brown Alan, Grigg Ronald, Ravishankar Thangavelauthum, Thornton-Pett Mark: Palladium catalysed cyclisation-cyclopropanation and cyclisation - anion capture processes of vinyl triflates. Tetrahetron Lett 1994, 35, 2753. <http://dx.doi.org/10.1016/S0040-4039(00)77024-9>
  • Meyer Christophe, Marek Ilane, Normant Jean-F., Platzer Nicole: Carbocyclization of δ-acetylenic propargylic zinc reagents. Tetrahetron Lett 1994, 35, 5645. <http://dx.doi.org/10.1016/S0040-4039(00)77269-8>
  • Catellani Marta, Chiusoli Gian Paolo, Fagnola Maria Chiara, Solari Giovanna: Intramolecular cyclization of ortho-iodophenyl 3-butenoate to 4-methylcoumarin: Catalysis by palladium complexes. Tetrahetron Lett 1994, 35, 5919. <http://dx.doi.org/10.1016/S0040-4039(00)78219-0>
  • Grigg Ronald, Redpath James, Sridharan Visuvanathar, Wilson David: Palladium catalysed cascade carbonylation-cyclisation-carbometallation-anion capture. Tetramolecular queuing processes. Tetrahetron Lett 1994, 35, 7661. <http://dx.doi.org/10.1016/S0040-4039(00)78369-9>
  • Clasby Martin C., Craig Donald, Marsh Andrew: Vitamin-D3-Synthesestudien: enantiospezifische Synthese des CD-Ring-Fragmentes von Vitamin D3. Angew Chem 1993, 105, 1495. <http://dx.doi.org/10.1002/ange.19931051018>
  • Clasby Martin C., Craig Donald, Marsh Andrew: Vitamin D3 Synthetic Studies: Enantiospecific Synthesis of the CD Ring Fragment. Angew Chem Int Ed Engl 1993, 32, 1444. <http://dx.doi.org/10.1002/anie.199314441>
  • Negishi Ei-ichi, Ay Mehmet, Sugihara Takumichi: Selective synthesis of benzene derivatives via palladium-catalyzed cascade carbometallation of alkynes. Tetrahedron 1993, 49, 5471. <http://dx.doi.org/10.1016/S0040-4020(01)87263-X>
  • Grigg Ronald, Kennewell Peter, Teasdale Andrew, Sridharan Visuvanathar: Palladium catalysed cascade cycloaddition reactions. General concepts and illustrative examples. Tetrahetron Lett 1993, 34, 153. <http://dx.doi.org/10.1016/S0040-4039(00)60081-3>
  • Grigg Ronald, Sridharan Visuvanathar: Spirocycles via palladium catalysed cascade cyclisation-carbonylation-anion capture processes. Tetrahetron Lett 1993, 34, 7471. <http://dx.doi.org/10.1016/S0040-4039(00)60156-9>
  • Semmelhack M.F., Epa W.R.: Catalytic tandem oxy-palladation and vinylation. Tetrahetron Lett 1993, 34, 7205. <http://dx.doi.org/10.1016/S0040-4039(00)79288-4>
  • Nuss John M., Murphy Martin M., Rennels Roger A., Heravi Magid H., Mohr Brent J.: Convergent approaches to the Vitamin D skeleton using a transition metal catalyzed carbometalation/capture strategy. Tetrahetron Lett 1993, 34, 3079. <http://dx.doi.org/10.1016/S0040-4039(00)93384-7>
  • Hoffmann H. Martin R.: Kaskaden-Cyclisierungen. Angew Chem 1992, 104, 1361. <http://dx.doi.org/10.1002/ange.19921041008>
  • Grigg Ronald, Kennewell Peter, Teasdale Andrew J: Palladium catalysed cascade cyclisation - carbonylation processes. Rate enhancement by Tl(I) salts. Tetrahetron Lett 1992, 33, 7789. <http://dx.doi.org/10.1016/0040-4039(93)88047-M>
  • Brocato Emanuela, Castagnoli Carlo, Catellani Marta, Chiusoli Gian Paolo: A new palladium-catalyzed synthesis of 3-substituted 2-aryliden-2,3-dihydro-1H-inden-1-ones. Tetrahetron Lett 1992, 33, 7433. <http://dx.doi.org/10.1016/S0040-4039(00)60208-3>
  • Grigg Ronald, Sridharan Visuvanathar: Palladium catalysed intermolecular cascade cyclisation - cyclopropanation reactions. Tetrahetron Lett 1992, 33, 7965. <http://dx.doi.org/10.1016/S0040-4039(00)74790-3>