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Pure Appl. Chem., 2004, Vol. 76, No. 3, pp. 589-601

http://dx.doi.org/10.1351/pac200476030589

Coordination of the Trost modular ligand to palladium allyl fragments: Oligomers, monomers and memory effects in catalysis

G. C. Lloyd-Jones, S. C. Stephen, I. J. S. Fairlamb, Aina Martorell, Beatriz Dominguez, P. M. Tomlin, M. Murray, J. M. Fernandez, J. C. Jeffery, T. Riis-Johannessen and Toufik Guerziz

The Bristol Centre for Organometallic Catalysis, School of Chemistry, The University of Bristol, Cantock ’s Close, Bristol, BS8 1TS, UK

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  • Uberman Paula M., Caira Mino R., Martı́n Sandra E.: A Chiral Bis(arsine) Ligand: Synthesis and Applications in Palladium-Catalyzed Asymmetric Allylic Alkylations. Organometallics 2013, 32, 3220. <http://dx.doi.org/10.1021/om400144s>
  • Wang Liang, Menche Dirk: Construction of Multisubstituted Tetrahydropyrans by a Domino Oxa-Michael/Tsuji–Trost Reaction. J. Org. Chem. 2012, 77, 10811. <http://dx.doi.org/10.1021/jo302102x>
  • Hoseini S. Jafar, Nasrabadi Hasan, Nabavizadeh S. Masoud, Rashidi Mehdi, Puddephatt Richard J.: Reactivity and Mechanism in the Oxidative Addition of Allylic Halides to a Dimethylplatinum(II) Complex. Organomettalics 2012, 31, 2357. <http://dx.doi.org/10.1021/om201289e>
  • Tsarev Vasily N., Wolters Dennis, Gais Hans-Joachim: Redox Reaction of the Pd0 Complex Bearing the Trost Ligand with meso-Cycloalkene-1,4-biscarbonates Leading to a Diamidato PdII Complex and 1,3-Cycloalkadienes: Enantioselective Desymmetrization Versus Catalyst Deactivation. Chem Eur J 2010, 16, 2904. <http://dx.doi.org/10.1002/chem.200902739>
  • Mahadik Geetanjali S., Hitchcock Shawn R.: Chiral, non-racemic diols, and α-amino acid-derived β-amino alcohols as templates for chiral catalysts in the Tsuji–Trost reaction. Tet Asymm 2010, 21, 33. <http://dx.doi.org/10.1016/j.tetasy.2009.12.011>
  • Wolfe Jesse A., Hitchcock Shawn R.: Palladium catalyzed asymmetric sulfonylation mediated chiral β-hydroxy- and β-(o-diphenylphosphino)benzoyloxy (o-diphenyl phosphino)benzamides. Tet Asymm 2010, 21, 2690. <http://dx.doi.org/10.1016/j.tetasy.2010.10.022>
  • Eastoe Julian, Fairlamb Ian J. S., Fernández-Hernández Jesús M., Filali Emane, Jeffery John C., Lloyd-Jones Guy C., Martorell Aina, Meadowcroft Antony, Norrby Per-Ola, Riis-Johannessen Thomas: Interrogation of a dynamic multi-catalyst ensemble in asymmetric catalysis. Faraday Disc 2010, 145, 27. <http://dx.doi.org/10.1039/b910022a>
  • Gillespie Jason A., Dodds Deborah L., Kamer Paul C. J.: Rational design of diphosphorus ligands – a route to superior catalysts. Dalton Trans 2010, 39, 2751. <http://dx.doi.org/10.1039/b913778e>
  • Nasser Nasser, Eisler Dana J., Puddephatt Richard J.: A chiral diphosphine as trans-chelate ligand and its relevance to catalysis. Chem Commun 2010, 46, 1953. <http://dx.doi.org/10.1039/b923911a>
  • Wang Chao, Pahadi Nirmal, Tunge Jon A.: Decarboxylative cyclizations and cycloadditions of palladium-polarized aza-ortho-xylylenes. Tetrahedron 2009, 65, 5102. <http://dx.doi.org/10.1016/j.tet.2009.04.071>
  • Benoit Wendy L., Parvez Masood, Keay Brian A.: Development of P-stereogenic 2-phenyl-1,3,2-oxazaphosphorine ligands and their unexpected sensitivity to oxidation. Tet Asymm 2009, 20, 69. <http://dx.doi.org/10.1016/j.tetasy.2008.12.027>
  • Butts Craig P., Filali Emane, Lloyd-Jones Guy C., Norrby Per-Ola, Sale David A., Schramm York: Structure-Based Rationale for Selectivity in the Asymmetric Allylic Alkylation of Cycloalkenyl Esters Employing the Trost ‘Standard Ligand’ (TSL): Isolation, Analysis and Alkylation of the Monomeric form of the Cationic η3-Cyclohexenyl Complex [(η3-c-C6H9)Pd(TSL)]+. J Am Chem Soc 2009, 131, 9945. <http://dx.doi.org/10.1021/ja8099757>
  • Braun Manfred, Meier Thorsten, Laicher Frank, Meletis Panos, Fidan Mesut: Palladium-Catalyzed Diastereoselective and Enantioselective Allylic Alkylations of Ketone Enolates. Adv Synth Catal 2008, 350, 303. <http://dx.doi.org/10.1002/adsc.200700409>
  • Kühnert Janett, Císařová Ivana, Lamač Martin, Štěpnička Petr: Group-12 metal complexes with isomeric 1-(diphenylphosphino)-1′-[N-(pyridylmethyl)carbamoyl]ferrocenes: coordination polymers vs. finite multinuclear coordination assemblies. Dalton Trans 2008, 2454. <http://dx.doi.org/10.1039/b719334c>
  • Lloyd-Jones Guy C., Muñoz M. Paz: Isotopic labelling in the study of organic and organometallic mechanism and structure: an account. J Labelled Cpd Radiopharm 2007, 50, 1072. <http://dx.doi.org/10.1002/jlcr.1382>
  • Kündig E. Peter, Chaudhuri Piyali Datta, House David, Bernardinelli Gérald: Catalytic Enantioselective Hydrogenolysis of [Cr(CO)3(5,8-Dibromonaphthalene)]. Angew Chem 2006, 118, 1110. <http://dx.doi.org/10.1002/ange.200502688>
  • Kündig E. Peter, Chaudhuri Piyali Datta, House David, Bernardinelli Gérald: Catalytic Enantioselective Hydrogenolysis of [Cr(CO)3(5,8-Dibromonaphthalene)]. Angew Chem Int Ed 2006, 45, 1092. <http://dx.doi.org/10.1002/anie.200502688>
  • Sturm Thomas, Abad Beatriz, Weissensteiner Walter, Mereiter Kurt, Manzano Blanca R., Jalón Félix A.: Palladium-catalysed allylic alkylations and aminations with hetero- and homoannularly bridged bidentate ferrocene ligands. Journal of Molecular Catalysis A 2006, 255, 209. <http://dx.doi.org/10.1016/j.molcata.2006.03.069>
  • Wysocki Laura M., Dodge Matthew W., Voight Eric A., Burke Steven D.: Stereochemically General Approach to Adjacent Bis(tetrahydrofuran) Cores of Annonaceous Acetogenins. Org Lett 2006, 8, 5637. <http://dx.doi.org/10.1021/ol062390l>
  • Pei Yuxin, Brulé Emilie, Moberg Christina: Modular multidentate phosphine ligands: application to palladium-catalyzed allylic alkylations. Org Biomol Chem 2006, 4, 544. <http://dx.doi.org/10.1039/b513906f>
  • Gais Hans-Joachim, Bondarev Oleg, Hetzer Ralf: Palladium-catalyzed asymmetric synthesis of allylic alcohols from unsymmetrical and symmetrical racemic allylic carbonates featuring C–O-bond formation and dynamic kinetic resolution. Tetrahetron Lett 2005, 46, 6279. <http://dx.doi.org/10.1016/j.tetlet.2005.07.044>
  • Lloyd-Jones Guy C., Stephen Susanna C., Fairlamb Ian J. S., Martorell Aina, Dominguez Beatriz, Tomlin Paula M., Murray Martin, Fernandez Jesus M., Jeffery John C., Riis-Johannessen Thomas: Coordination of the Trost Modular Ligand to Palladium Allyl Fragments: Oligomers, Monomers, and Memory Effects in Catalysis. ChemInform 2004, 35. <http://dx.doi.org/10.1002/chin.200439253>