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Pure Appl. Chem., 1997, Vol. 69, No. 3, pp. 513-518

http://dx.doi.org/10.1351/pac199769030513

Enantioselective catalysis with complexes of asymmetric P,N-chelate ligands

G. Helmchen, Steffen Kudis, P. Sennhenn and H. Steinhagen

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  • Farkas Gergely, Császár Zsófia, Balogh Szabolcs, Szöllősy Áron, Gouygou Maryse, Bakos József: Phosphine–phosphite ligands in the palladium-catalyzed asymmetric allylic alkylation: Electronic and steric effects. Catalysis Communications 2013, 36, 94. <http://dx.doi.org/10.1016/j.catcom.2013.03.005>
  • Bratko Ielyzaveta, Gómez Montserrat: Polymetallic complexes linked to a single-frame ligand: cooperative effects in catalysis. Dalton Trans. 2013, 42, 10664. <http://dx.doi.org/10.1039/c3dt50963j>
  • Bellini Rosalba, Reek Joost N. H.: Supramolecular Hybrid Bidentate Ligands in Asymmetric Hydrogenation. Eur. J. Inorg. Chem. 2012, 2012, 4684. <http://dx.doi.org/10.1002/ejic.201200549>
  • Shi Ce, Chien Chih-Wei, Ojima Iwao: Synthesis of Chiral Biphenol-Based Diphosphonite Ligands and Their Application in Palladium-Catalyzed Intermolecular Asymmetric Allylic Amination Reactions. Chem Asian J 2011, 6, 674. <http://dx.doi.org/10.1002/asia.201000697>
  • 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>
  • Wassenaar Jeroen, Reek Joost N. H.: Hybrid bidentate phosphorus ligands in asymmetric catalysis: Privileged ligand approach vs. combinatorial strategies. Org Biomol Chem 2011, 9, 1704. <http://dx.doi.org/10.1039/c0ob00732c>
  • Böttcher Benjamin, Schmidts Volker, Raskatov Jevgenij A., Thiele Christina M.: Bestimmung der Konformation des Schlüsselintermediats einer enantioselektiven Palladium-katalysierten allylischen Substitution mithilfe dipolarer Restkopplungen. angew chemie 2010, 122, 210. <http://dx.doi.org/10.1002/ange.200903649>
  • Böttcher Benjamin, Schmidts Volker, Raskatov Jevgenij A., Thiele Christina M.: Determination of the Conformation of the Key Intermediate in an Enantioselective Palladium-Catalyzed Allylic Substitution from Residual Dipolar Couplings. Angew Chem Int E 2010, 49, 205. <http://dx.doi.org/10.1002/anie.200903649>
  • Mazuela Javier, Paptchikhine Alexander, Tolstoy Päivi, Pàmies Oscar, Diéguez Montserrat, Andersson Pher G.: A New Class of Modular P,N-Ligand Library for Asymmetric Pd-Catalyzed Allylic Substitution Reactions: A Study of the Key Pd–π-Allyl Intermediates. Chem Eur J 2010, 16, 620. <http://dx.doi.org/10.1002/chem.200901842>
  • HELMCHEN G., KUDIS S., SENNHENN P., STEINHAGEN H.: ChemInform Abstract: Enantioselective Catalysis with Complexes of Asymmetric P,N-Chelate Ligands. ChemInform 2010, 28, no. <http://dx.doi.org/10.1002/chin.199730290>
  • Dorneles Luciano, Braga Antonio L., Sehnem Jasquer A., Milani Priscila, Nascimento Vanessa, Andrade Leandro H.: Synthesis of new fluorous modular chiral ligand derivatives from amino alcohols and application in enantioselective carbon–carbon bond-forming alkylation reactions. Tet Asymm 2010, 21, 997. <http://dx.doi.org/10.1016/j.tetasy.2010.05.015>
  • Wang Yu, Hämäläinen Antti, Tois Jan, Franzén Robert: Preparation of indole-phosphine oxazoline (IndPHOX) ligands and their application in allylic alkylation. Tet Asymm 2010, 21, 2376. <http://dx.doi.org/10.1016/j.tetasy.2010.08.008>
  • McDougal Nolan T., Streuff Jan, Mukherjee Herschel, Virgil Scott C., Stoltz Brian M.: Rapid synthesis of an electron-deficient t-BuPHOX ligand: cross-coupling of aryl bromides with secondary phosphine oxides. Tetrahetron Lett 2010, 51, 5550. <http://dx.doi.org/10.1016/j.tetlet.2010.08.039>
  • Raluy Eva, Pàmies Oscar, Diéguez Montserrat: Modular Furanoside Phosphite-Phosphoroamidites, a Readily Available Ligand Library for Asymmetric Palladium-Catalyzed Allylic Substitution Reactions. Origin of Enantioselectivity. Adv Synth Catal 2009, 351, 1648. <http://dx.doi.org/10.1002/adsc.200900073>
  • Mata Yvette, Pàmies Oscar, Diéguez Montserrat: Pyranoside Phosphite-Oxazoline Ligand Library: Highly Efficient Modular P,N Ligands for Palladium-Catalyzed Allylic Substitution Reactions. A Study of the Key Palladium Allyl Intermediates. Adv Synth Catal 2009, 351, 3217. <http://dx.doi.org/10.1002/adsc.200900619>
  • Lorcy Dominique, Bellec Nathalie, Fourmigué Marc, Avarvari Narcis: Tetrathiafulvalene-based group XV ligands: Synthesis, coordination chemistry and radical cation salts. Coord Chem Rev - 2009, 253, 1398. <http://dx.doi.org/10.1016/j.ccr.2008.09.012>
  • Diéguez Montserrat, Pàmies Oscar: Modular Phosphite–Oxazoline/Oxazine Ligand Library for Asymmetric Pd-Catalyzed Allylic Substitution Reactions: Scope and Limitations—Origin of Enantioselectivity. Chem Eur J 2008, 14, 3653. <http://dx.doi.org/10.1002/chem.200701636>
  • Šebesta Radovan, Bilčík Filip, Horváth Branislav: [3]Ferrocenophane Ligands with an Inserted Methylene Group. Eur J Org Chem 2008, 2008, 5157. <http://dx.doi.org/10.1002/ejoc.200800566>
  • Liu Delong, Xie Fang, Zhao Xiaohu, Zhang Wanbin: Enantioselective transfer hydrogenation of ketones with planar chiral ruthenocene-based phosphinooxazoline ligands. Tetrahedron 2008, 64, 3561. <http://dx.doi.org/10.1016/j.tet.2008.01.108>
  • Andrade Leandro H., Silva Alexandre V.: First chemoenzymatic synthesis of organoselenium amines and amides. Tet Asymm 2008, 19, 1175. <http://dx.doi.org/10.1016/j.tetasy.2008.04.026>
  • Drommi Dario, Saporita Maria, Bruno Giuseppe, Faraone Felice, Scafato Patrizia, Rosini Carlo: Origin of enantioselectivity in palladium-catalyzed asymmetric allylic alkylation reactions using chiral N,N-ligands with different rigidity and flexibility. Dalton Trans 2007, 1509. <http://dx.doi.org/10.1039/b618347f>
  • Goldfuss Bernd: Electronic differentiations in palladium-catalyzed allylic substitutions. J Organomet Chem 2006, 691, 4508. <http://dx.doi.org/10.1016/j.jorganchem.2006.01.061>
  • Trudeau Stéphane, Morken James P.: StePHOX, a new family of optically active, tunable phosphine–oxazoline ligands: syntheses and applications. Tetrahedron 2006, 62, 11470. <http://dx.doi.org/10.1016/j.tet.2006.05.043>
  • Réthoré Céline, Suisse Isabelle, Agbossou-Niedercorn Francine, Guillamón Eva, Llusar Rosa, Fourmigué Marc, Avarvari Narcis: Chiral tetrathiafulvalene based phosphine- and thiomethyl-oxazoline ligands. Evaluation in palladium catalysed asymmetric allylic alkylation. Tetrahedron 2006, 62, 11942. <http://dx.doi.org/10.1016/j.tet.2006.09.088>
  • 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>
  • Braga Antonio L., Lüdtke Diogo S., Sehnem Jasquer A., Alberto Eduardo E.: Modular chiral selenium-containing oxazolines: synthesis and application in the palladium-catalyzed asymmetric allylic alkylation. Tetrahedron 2005, 61, 11664. <http://dx.doi.org/10.1016/j.tet.2005.09.044>
  • Tang Dianyong, Luo Xiaoling, Shen Wei, Li Ming: The mechanism of enantioselective palladium(0)-catalyzed allylic alkylation with chiral oxazolinylpyridines: a DFT study. Journal of Molecular Structure: THEOCHEM 2005, 716, 79. <http://dx.doi.org/10.1016/j.theochem.2004.10.087>
  • Goldfuss Bernd, Löschmann Thomas, Rominger Frank: Ligand Bite Governs Enantioselectivity: Electronic and Steric Control in Pd-Catalyzed Allylic Alkylations by Modular Fenchyl Phosphinites (FENOPs). Chem Eur J 2004, 10, 5422. <http://dx.doi.org/10.1002/chem.200400273>
  • Guiu Ester, Claver Carmen, Castillón Sergio: Ir(I) complexes with oxazoline-thioether ligands: nucleophilic attack of pyridine on coordinated 1,5-cyclooctadiene and application as catalysts in imine hydrogenation. J Organomet Chem 2004, 689, 1911. <http://dx.doi.org/10.1016/j.jorganchem.2004.03.015>
  • Berkowitz David B., Shen Weijun, Maiti Gourhari: In situ enzymatic screening (ISES) of P,N-ligands for Ni(0)-mediated asymmetric intramolecular allylic amination. Tet Asymm 2004, 15, 2845. <http://dx.doi.org/10.1016/j.tetasy.2004.06.052>
  • Guiu Ester, Claver Carmen, Benet-Buchholz Jordi, Castillón Sergio: An efficient method for the synthesis of enantiopure phosphine–imidazoline ligands: application to the Ir-catalyzed hydrogenation of imines. Tet Asymm 2004, 15, 3365. <http://dx.doi.org/10.1016/j.tetasy.2004.09.013>
  • 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>
  • Schinnerl Marina, Böhm Claudius, Seitz Michael, Reiser Oliver: New bis(oxazoline) ligands with secondary binding sites for the asymmetric cyclopropanation of furans. Tet Asymm 2003, 14, 765. <http://dx.doi.org/10.1016/S0957-4166(03)00094-6>
  • Zehnder Margareta, Neuburger Markus, Schaffner Silvia, Jufer Martin, Plattner Dietmar A.: Synthesis, X-ray Structures, NMR Studies and Density Functional Calculations of (η2-Fumarodinitrile)palladium(0) Complexes Containing Dihydro(phosphanylphenyl)oxazole Ligands. Eur J Inorg Chem 2002, 2002, 1511. <http://dx.doi.org/10.1002/1099-0682(200206)2002:6<1511::AID-EJIC1511>3.0.CO;2-C>
  • Mandal Swadhin K., Nagana Gowda G. A., Krishnamurthy Setharampattu S., Zheng Chong, Li Shoujian, Hosmane Narayan S.: Allylpalladium Complexes of Mixed-Donor Diphosphazane Ligands Bearing a Stereogenic Phosphorus Centre: Structure and Stereodynamics. Eur J Inorg Chem 2002, 2002, 2047. <http://dx.doi.org/10.1002/1099-0682(200208)2002:8<2047::AID-EJIC2047>3.0.CO;2-R>
  • Carmona Daniel, Ferrer Joaquina, Lalaguna Elena, Lorenzo Mónica, Lahoz Fernando J., Elipe Sergio, Oro Luis A.: Preparation and Properties of RhI and IrI Ethylene Complexes Containing the ChiralP,N-Chelate Ligand (4S)-2-[2-(Diphenylphosphanyl)phenyl]-4-isopropyl-1,3-oxazoline. Eur J Inorg Chem 2002, 2002, 259. <http://dx.doi.org/10.1002/1099-0682(20021)2002:1<259::AID-EJIC259>3.0.CO;2-T>
  • Zehnder Margareta, Schaffner Silvia, Neuburger Markus, Plattner Dietmar A: X-ray crystallographic and NMR spectroscopical characterization of intermediates in the Pd-catalyzed allylic substitution reaction with 4-substituted phosphinooxazolines. Correlation between intermediate structure and product configuration. Inorganica Chimica Acta 2002, 337, 287. <http://dx.doi.org/10.1016/S0020-1693(02)00998-2>
  • Patti Angela, Lotz Matthias, Knochel Paul: Synthesis of α,β-disubstituted ferrocenes via a ferrocenylepoxide intermediate. Preparation and catalytic activity of a new chiral ferrocenyloxazoline. Tet Asymm 2002, 12, 3375. <http://dx.doi.org/10.1016/S0957-4166(02)00036-8>
  • Figge Axel, Altenbach Hans J., Brauer David J., Tielmann Patrick: Synthesis and resolution of 2-(2-diphenylphosphinyl-naphthalen-1-yl)-1-isopropyl-1H-benzoimidazole; a new atropisomeric P,N-chelating ligand for asymmetric catalysis. Tet Asymm 2002, 13, 137. <http://dx.doi.org/10.1016/S0957-4166(02)00079-4>
  • Bolm Carsten, Kesselgruber Martin, Hermanns Nina, Hildebrand Jens P., Raabe Gerhard: Application of a Planar Chiralη5-Cyclopentadienylrhenium(I)tricarbonyl Complex in Asymmetric Catalysis: Highly Enantioselective Phenyl Transfer to Aldehydes. Angew Chem 2001, 113, 1536. <http://dx.doi.org/10.1002/1521-3757(20010417)113:8<1536::AID-ANGE1536>3.0.CO;2-D>
  • Bolm Carsten, Kesselgruber Martin, Hermanns Nina, Hildebrand Jens P., Raabe Gerhard: Application of a Planar Chiralη5-Cyclopentadienylrhenium(I)tricarbonyl Complex in Asymmetric Catalysis: Highly Enantioselective Phenyl Transfer to Aldehydes. Angew Chem Int Ed 2001, 40, 1488. <http://dx.doi.org/10.1002/1521-3773(20010417)40:8<1488::AID-ANIE1488>3.0.CO;2-B>
  • Gilbertson Scott R, Fu Zice, Xie Dejian: Proline derived phosphine–oxazoline ligands in the asymmetric Heck reaction. Tetrahetron Lett 2001, 42, 365. <http://dx.doi.org/10.1016/S0040-4039(00)01938-9>
  • Bergner Eike J., Helmchen Günter: Synthesis of Enantiomerically Pure (−)-Wine Lactone Based on a Palladium-Catalyzed Enantioselective Allylic Substitution. Eur J Org Chem 2000, 2000, 419. <http://dx.doi.org/10.1002/(SICI)1099-0690(200002)2000:3<419::AID-EJOC419>3.0.CO;2-N>
  • Dübner Frank, Knochel Paul: Highly enantioselective copper-catalyzed substitution of allylic chlorides with diorganozincs. Tetrahetron Lett 2000, 41, 9233. <http://dx.doi.org/10.1016/S0040-4039(00)01671-3>
  • Pfaltz Andreas: Chiral heterocycles as ligands in asymmetric catalysis. J Heterocyclic Chem 1999, 36, 1437. <http://dx.doi.org/10.1002/jhet.5570360607>
  • Hunger J., Huttner G.: Optimization and analysis of force field parameters by combination of genetic algorithms and neural networks. J Comput Chem 1999, 20, 455. <http://dx.doi.org/10.1002/(SICI)1096-987X(199903)20:4<455::AID-JCC6>3.0.CO;2-1>
  • Schleich Simone, Helmchen Günter: Pd-Catalyzed Asymmetric Allylic Alkylation of 3-Acetoxy-N-(tert-butyloxycarbonyl)-1,2,3,6-tetrahydropyridine – Preparation of Key Intermediates for Natural Product Synthesis. Eur J Org Chem 1999, 1999, 2515. <http://dx.doi.org/10.1002/(SICI)1099-0690(199910)1999:10<2515::AID-EJOC2515>3.0.CO;2-G>
  • Gilbertson Scott R., Xie Dejian: P,N-Liganden auf Prolinbasis in Palladium-katalysierten asymmetrischen π-Allyl-Additionen. Angew Chem 1999, 111, 2915. <http://dx.doi.org/10.1002/(SICI)1521-3757(19990917)111:18<2915::AID-ANGE2915>3.0.CO;2-F>
  • Gómez Montserrat, Muller Guillermo, Rocamora Mercè: Coordination chemistry of oxazoline ligands. Coord Chem Rev - 1999, 193-195, 769. <http://dx.doi.org/10.1016/S0010-8545(99)00086-7>
  • Flubacher Dietmar, Helmchen Günter: Enantioselective domino Heck-allylic amination reactions. Tetrahetron Lett 1999, 40, 3867. <http://dx.doi.org/10.1016/S0040-4039(99)00628-0>
  • Schaffner Silvia, Müller Jürgen F. K., Neuburger Markus, Zehnder Margareta: On the Origin of Asymmetric Induction of the Palladium-Catalyzed Allylic Substitution Reaction with Chiral 4,4-Disubstituted 4,5-Dihydro-2-(phosphinoaryl)oxazole Ligands. HCA 1998, 81, 1223. <http://dx.doi.org/10.1002/hlca.19980810533>
  • Hunger Johannes, Beyreuther Stefan, Huttner Gottfried, Allinger Kurt, Radelof Uwe, Zsolnai Laszlo: How to Derive Force Field Parameters by Genetic Algorithms: Modellingtripod-Mo(CO)3 Compounds as an Example. Eur J Inorg Chem 1998, 1998, 693. <http://dx.doi.org/10.1002/(SICI)1099-0682(199806)1998:6<693::AID-EJIC693>3.0.CO;2-M>
  • Prétôt Roger, Pfaltz Andreas: Neue Liganden für die Steuerung der Regio- und Enantioselektivität von Pd-katalysierten allylischen Alkylierungen. Angew Chem 1998, 110, 337. <http://dx.doi.org/10.1002/(SICI)1521-3757(19980202)110:3<337::AID-ANGE337>3.0.CO;2-N>
  • Hegedus Louis S.: Transition metals in organic synthesis, highlights for the year 1997. Coord Chem Rev - 1998, 175, 159. <http://dx.doi.org/10.1016/S0010-8545(98)00138-6>
  • Lloyd-Jones Guy C., Butts Craig P.: Nickel (II) complexes bearing phosphinoaryl oxazoline ligands as pro-catalysts for Grignard cross-coupling. Tetrahedron 1998, 54, 901. <http://dx.doi.org/10.1016/S0040-4020(97)10332-5>
  • Kudis Steffen, Helmchen Günter: First enantioselective synthesis of (+)-(3R,3aS,6aS)-3-hydroxy-3,3a,4,6a-tetrahydrocyclopenta[b]furan-2-one — a versatile chiral heterocyclic building block. Tetrahedron 1998, 54, 10449. <http://dx.doi.org/10.1016/S0040-4020(98)00497-9>
  • Wiese Burkhard, Helmchen Günter: Chiral phosphinooxazolines with a bi- or tricyclic oxazoline moiety - applications in Pd-catalyzed allylic alkylations. Tetrahetron Lett 1998, 39, 5727. <http://dx.doi.org/10.1016/S0040-4039(98)01173-3>
  • Liu Shuangying, Müller Jürgen F.K., Neuburger Markus, Schaffner Silvia, Zehnder Margareta: Crystallographic studies of {η3-1,3-dimethylallyl}{2-[2′-diphenylphosphino) phenyl]oxazoline-P,N} palladium(II) hexafluorophosphates complexes complemented by 1H NMR investigations. J Organomet Chem 1997, 549, 283. <http://dx.doi.org/10.1016/S0022-328X(97)00509-3>