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Pure Appl. Chem., 1999, Vol. 71, No. 8, pp. 1425-1433

http://dx.doi.org/10.1351/pac199971081425

Transition metal catalysis in organic synthesis: reflections, chirality and new vistas

Pavel Kočovský, Andrei V. Malkov, Štěpán Vyskočil and Guy C. Lloyd-Jones

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  • Malkov Andrei V., Derrien Nolwenn, Barłóg Maciej, Kočovský Pavel: Palladium-Catalyzed Alkoxycarbonylation of Terminal Alkenes To Produce α,β-Unsaturated Esters: The Key Role of Acetonitrile as a Ligand. Chem. Eur. J. 2014, 20, 4542. <http://dx.doi.org/10.1002/chem.201304798>
  • Malkov Andrei V., Barłóg Maciej, Miller-Potucká Lucie, Kabeshov Mikhail A., Farrugia Louis J., Kočovský Pavel: Stereoselective Palladium-Catalyzed Functionalization of Homoallylic Alcohols: A Convenient Synthesis of Di- and Trisubstituted Isoxazolidines and β-Amino-δ-Hydroxy Esters. Chem. Eur. J. 2012, 18, 6873. <http://dx.doi.org/10.1002/chem.201102716>
  • Chen David Y.-K., Youn So Won: CH Activation: A Complementary Tool in the Total Synthesis of Complex Natural Products. Chem. Eur. J. 2012, 18, 9452. <http://dx.doi.org/10.1002/chem.201201329>
  • Lu Chun, Dubrovskiy Anton V., Larock Richard C.: Palladium-Catalyzed Annulation of Arynes by o-Halobenzamides: Synthesis of Phenanthridinones. J. Org. Chem. 2012, 77, 8648. <http://dx.doi.org/10.1021/jo3016192>
  • Lu Chun, Markina Nataliya A., Larock Richard C.: Synthesis of N-Acylcarbazoles through Palladium-Catalyzed Aryne Annulation of 2-Haloacetanilides. J. Org. Chem. 2012, 77, 11153. <http://dx.doi.org/10.1021/jo3021727>
  • Chelucci Giorgio, Marchetti Mauro, Malkov Andrei V., Friscourt Frédéric, Swarbrick Martin E., Kočovský Pavel: New monoterpene-derived phosphinopyridine ligands and their application in the enantioselective iridium-catalyzed hydrogenation. Tetrahedron 2011, 67, 5421. <http://dx.doi.org/10.1016/j.tet.2011.05.075>
  • Štambaský Jan, Kapras Vojtěch, Štefko Martin, Kysilka Ondřej, Hocek Michal, Malkov Andrei V., Kočovský Pavel: A Modular Approach to Aryl-C-ribonucleosides via the Allylic Substitution and Ring-Closing Metathesis Sequence. A Stereocontrolled Synthesis of All Four α-/β- and d-/l-C-Nucleoside Stereoisomers. J Org Chern 2011, 76, 7781. <http://dx.doi.org/10.1021/jo201110z>
  • Osswald Tina, Mikhel Igor S., Rüegger Heinz, Butti Pietro, Mezzetti Antonio: Secondary ligand–metal interactions in rhodium(III) and iridium(III) phosphoramidite complexes. Inorg Chim Ada 2010, 363, 474. <http://dx.doi.org/10.1016/j.ica.2009.05.008>
  • Onitsuka Kiyotaka, Okuda Haruki, Sasai Hiroaki: Regio- and Enantioselective O-Allylation of Phenol and Alcohol Catalyzed by a Planar-Chiral Cyclopentadienyl Ruthenium Complex. Angew Chem 2008, 120, 1476. <http://dx.doi.org/10.1002/ange.200704457>
  • Onitsuka Kiyotaka, Okuda Haruki, Sasai Hiroaki: Regio- and Enantioselective O-Allylation of Phenol and Alcohol Catalyzed by a Planar-Chiral Cyclopentadienyl Ruthenium Complex. Angew Chem Int Ed 2008, 47, 1454. <http://dx.doi.org/10.1002/anie.200704457>
  • Malkov Andrei V., Gouriou Laure, Lloyd-Jones Guy C., Starý Ivo, Langer Vratislav, Spoor Paul, Vinader Victoria, Kočovský Pavel: Asymmetric Allylic Substitution Catalyzed byC1-Symmetrical Complexes of Molybdenum: Structural Requirements of the Ligand and the Stereochemical Course of the Reaction. Chem Eur J 2006, 12, 6910. <http://dx.doi.org/10.1002/chem.200501574>
  • Patil Nitin T., Song Dschun, Yamamoto Yoshinori: Palladium-Catalyzed Allylation of Pronucleophiles with Alkynes at 50 °C – Remarkable Effect of 2-(Dicyclohexylphosphanyl)-2′-(dimethylamino)biphenyl as Ligand. Eur J Org Chem 2006, 2006, 4211. <http://dx.doi.org/10.1002/ejoc.200600337>
  • Malkov Andrei V., Stončius Sigitas, MacDougall Kenneth N., Mariani Andrea, McGeoch Grant D., Kočovský Pavel: Formamides derived from N-methyl amino acids serve as new chiral organocatalysts in the enantioselective reduction of aromatic ketimines with trichlorosilane. Tetrahedron 2006, 62, 264. <http://dx.doi.org/10.1016/j.tet.2005.08.117>
  • Luft Jennifer A.R., Yu Zhi-Xiang, Hughes David L., Lloyd-Jones Guy C., Krska Shane W., Houk Kendall N.: On the stability of the π-allyl intermediate in molybdenum-catalyzed asymmetric alkylations. Tet Asymm 2006, 17, 716. <http://dx.doi.org/10.1016/j.tetasy.2006.01.037>
  • Chen Chuan-Lin, Liu Yi-Hung, Peng Shie-Ming, Liu Shiuh-Tzung: An efficient catalyst for Suzuki–Miyaura coupling reaction in aqueous medium under aerobic conditions. Tetrahetron Lett 2005, 46, 521. <http://dx.doi.org/10.1016/j.tetlet.2004.10.177>
  • Hughes D. L., Lloyd-Jones G. C., Krska S. W., Gouriou L., Bonnet V. D., Jack K., Sun Y., Mathre D. J., Reamer R. A.: Asymmetric Catalysis Special Feature Part I: Mechanistic studies of the molybdenum-catalyzed asymmetric alkylation reaction. Proceedings of the National Academy of Sciences 2004, 101, 5379. <http://dx.doi.org/10.1073/pnas.0306918101>
  • Kočovský Pavel: Reactivity control in palladium-catalyzed reactions: a personal account. J Organomet Chem 2003, 687, 256. <http://dx.doi.org/10.1016/j.jorganchem.2003.07.008>
  • Gouriou Laure, Lloyd-Jones Guy C, Vyskočil Štěpán, Kočovský Pavel: 2H-quadrupolar coupling-based analysis of stereochemical and regiochemical memory in the Pd-catalysed allylic alkylation of iso-cinnamyl type substrates employing the chiral monophosphine ligands ‘MOP’ and ‘MAP’. J Organomet Chem 2003, 687, 525. <http://dx.doi.org/10.1016/j.jorganchem.2003.09.015>
  • Kawamura Masato, Kiyotake Ryosuke, Kudo Kazuaki: Synthesis of a novel photoresponsive axially chiral phosphine ligand containing an arylazo group and its application to palladium-catalyzed asymmetric allylic alkylation. Chirality 2002, 14, 724. <http://dx.doi.org/10.1002/chir.10131>
  • Wang Yi, Li Xin, Ding Kuiling: The synthesis of a new generation of MAP ligands containing two types of chiral elements for asymmetric catalysis. Tetrahetron Lett 2002, 43, 159. <http://dx.doi.org/10.1016/S0040-4039(01)02056-1>
  • Wang Yi, Li Xin, Ding Kuiling: Synthesis of a new type of chiral amino phosphine ligands for asymmetric catalysis. Tet Asymm 2002, 13, 1291. <http://dx.doi.org/10.1016/S0957-4166(02)00324-5>
  • Kasák P, Mikláš R, Putala M: Study on the synthesis of nonracemic C2-symmetric 1,1′-binaphthyl-2,2′-diyl bridged ferrocene. Stereochemical result of the cross-coupling reactions controlled by Pd(II) or Pd(IV) complex intermediacy. J Organomet Chem 2001, 637-639, 318. <http://dx.doi.org/10.1016/S0022-328X(01)00926-3>