CrossRef enabled

PAC Archives

Archive →

Pure Appl. Chem., 2006, Vol. 78, No. 2, pp. 501-509

http://dx.doi.org/10.1351/pac200678020501

Rhodium-catalyzed asymmetric hydrogenation using self-assembled chiral bidentate ligands

James M. Takacs, Kittichai Chaiseeda, Shin A. Moteki, D. Sahadeva Reddy, Di Wu and Kusumlata Chandra

Department of Chemistry, University of Nebraska-Lincoln, Lincoln, NE 68588, USA

CrossRef Cited-by theme picture

CrossRef Cited-by Linking

  • Raynal Matthieu, Ballester Pablo, Vidal-Ferran Anton, van Leeuwen Piet W. N. M.: Supramolecular catalysis. Part 1: non-covalent interactions as a tool for building and modifying homogeneous catalysts. Chem. Soc. Rev. 2014, 43, 1660. <http://dx.doi.org/10.1039/c3cs60027k>
  • Frank Dominik J., Franzke Axel, Pfaltz Andreas: Asymmetric Hydrogenation Using Rhodium Complexes Generated from Mixtures of Monodentate Neutral and Anionic Phosphorus Ligands. Chem. Eur. J. 2013, 19, 2405. <http://dx.doi.org/10.1002/chem.201202408>
  • Kokan Zoran, Kirin Srećko I.: “Backdoor Induction” of Chirality in Asymmetric Hydrogenation with Rhodium(I) Complexes of Amino Acid Substituted Triphenylphosphane Ligands. Eur. J. Org. Chem. 2013, 2013, 8154. <http://dx.doi.org/10.1002/ejoc.201301011>
  • Kluwer Alexander M., Detz Remko J., Abiri Zohar, van der Burg Alida M., Reek Joost N. H.: Evolutionary Catalyst Screening: Iridium-Catalyzed Imine Hydrogenation. Adv. Synth. Catal. 2012, 354, 89. <http://dx.doi.org/10.1002/adsc.201100422>
  • Pignataro Luca, Boghi Michele, Civera Monica, Carboni Stefano, Piarulli Umberto, Gennari Cesare: Rhodium-Catalyzed Asymmetric Hydrogenation of Olefins with PhthalaPhos, a New Class of Chiral Supramolecular Ligands. Chemistry A European Journal 2012, 18, 1383. <http://dx.doi.org/10.1002/chem.201102018>
  • Bellini Rosalba, van der Vlugt Jarl Ivar, Reek Joost N. H.: Supramolecular Self-Assembled Ligands in Asymmetric Transition Metal Catalysis. Isr. J. Chem. 2012, 52, 613. <http://dx.doi.org/10.1002/ijch.201200002>
  • Thacker Nathan C., Moteki Shin A., Takacs James M.: Ligand Scaffold Optimization of a Supramolecular Hydrogenation Catalyst: Analyzing the Influence of Key Structural Subunits on Reactivity and Selectivity. ACS Catal. 2012, 2, 2743. <http://dx.doi.org/10.1021/cs300465u>
  • Moteki Shin A., Toyama Kazuya, Liu Zeyu, Ma Jing, Holmes Andrea E., Takacs James M.: Two-stage optimization of a supramolecular catalyst for catalytic asymmetric hydroboration. Chem Commn 2012, 48, 263. <http://dx.doi.org/10.1039/c1cc16146f>
  • Legrand François-Xavier, Menuel Stéphane, Bricout Hervé, Tilloy Sébastien, Monflier Eric, Tran Diem Ngan: Cyclodextrin–phosphane possessing a guest-tunable conformation for aqueous rhodium-catalyzed hydroformylation. Chem Commn 2012, 48, 753. <http://dx.doi.org/10.1039/c1cc16326d>
  • Kokan Zoran, Kirin Srećko I.: The application of “backdoor induction” in bioinspired asymmetric catalysis. RSC Adv. 2012, 2, 5729. <http://dx.doi.org/10.1039/c2ra20598j>
  • Freixa Zoraida, Ponsico Sergio, Frischmann Peter D., MacLachlan Mark J., Martfnez-Belmonte Marta, Escudero-Adán Eduardo C., van Leeuwen Piet W. N. M.: Bidentate ligands templated by a convex trimetallic bis(salphen) platform. Supramolecular Catalysis 2012, 1, 1. <http://dx.doi.org/10.2478/supcat-2012-0001>
  • Friest Jacob A., Broussy Sylvain, Chung Woo Jin, Berkowitz David B.: Combinatorial Catalysis Employing a Visible Enzymatic Beacon in Real Time: Synthetically Versatile (Pseudo)Halometalation/Carbocyclizations. angew chemie 2011, 123, 9057. <http://dx.doi.org/10.1002/ange.201103365>
  • Friest Jacob A., Broussy Sylvain, Chung Woo Jin, Berkowitz David B.: Combinatorial Catalysis Employing a Visible Enzymatic Beacon in Real Time: Synthetically Versatile (Pseudo)Halometalation/Carbocyclizations. Angew Chem Int E 2011, 50, 8895. <http://dx.doi.org/10.1002/anie.201103365>
  • Carboni Stefano, Gennari Cesare, Pignataro Luca, Piarulli Umberto: Supramolecular ligand–ligand and ligand–substrate interactions for highly selective transition metal catalysis. Dalton Trans 2011, 40, 4355. <http://dx.doi.org/10.1039/c0dt01517b>
  • Bauer Gernot, Benkő Zoltán, Nuss Jürgen, Nieger Martin, Gudat Dietrich: Assembly and Disassembly of a Metastable Bis-phosphine-Based Copper(I) Helicate. Chem Eur J 2010, 16, 12091. <http://dx.doi.org/10.1002/chem.201001414>
  • Meeuwissen Jurjen, Detz Remko, Sandee Albertus J., de Bruin Bas, Siegler Maxime A., Spek Anthony L., Reek Joost N. H.: Ureaphosphanes as Hybrid, Anionic or Supramolecular Bidentate Ligands for Asymmetric Hydrogenation Reactions. Eur J Inorg Chem 2010, 2010, 2992. <http://dx.doi.org/10.1002/ejic.201000213>
  • Meeuwissen Jurjen, Reek Joost N. H.: Supramolecular catalysis beyond enzyme mimics. Nature Chem 2010, 2, 615. <http://dx.doi.org/10.1038/nchem.744>
  • Meeuwissen Jurjen, Detz Remko J., Sandee Albertus J., de Bruin Bas, Reek Joost N. H.: Rhodium-P,O-bidentate coordinated ureaphosphine ligands for asymmetric hydrogenation reactions. Dalton Trans 2010, 39, 1929. <http://dx.doi.org/10.1039/b926043a>
  • Chikkali Samir H., Nieger Martin, Gudat Dietrich: Stoichiometry controlled self-assembly of tri- and octa-nuclear palladium–yttrium complexes. New J Chem 2010, 34, 1348. <http://dx.doi.org/10.1039/c0nj00020e>
  • Breuil Pierre-Alain R., Patureau Frederic W., Reek Joost N. H.: Singly Hydrogen Bonded Supramolecular Ligands for Highly Selective Rhodium-Catalyzed Hydrogenation Reactions. Angew Chem 2009, 121, 2196. <http://dx.doi.org/10.1002/ange.200806177>
  • Breuil Pierre-Alain R., Patureau Frederic W., Reek Joost N. H.: Singly Hydrogen Bonded Supramolecular Ligands for Highly Selective Rhodium-Catalyzed Hydrogenation Reactions. Angew Chem Int Ed 2009, 48, 2162. <http://dx.doi.org/10.1002/anie.200806177>
  • Chikkali Samir H., Gudat Dietrich, Lissner Falk, Niemeyer Mark, Schleid Thomas, Nieger Martin: Template-Controlled Assembly of Ditopic Catechol Phosphines: A Strategy for the Generation of Complexes of Bidentate Phosphines with Different Bite Angles. Chem. Eur. J. 2009, 15, 482. <http://dx.doi.org/10.1002/chem.200801517>
  • Meeuwissen Jurjen, Kuil Mark, van der Burg Alida M., Sandee Albertus J., Reek Joost N. H.: Application of a Supramolecular-Ligand Library for the Automated Search for Catalysts for the Asymmetric Hydrogenation of Industrially Relevant Substrates. Chem Eur J 2009, 15, 10272. <http://dx.doi.org/10.1002/chem.200901110>
  • Pignataro Luca, Lynikaite Benita, Cvengroš Ján, Marchini Mattia, Piarulli Umberto, Gennari Cesare: Combinations of Acidic and Basic Monodentate Binaphtholic Phosphites as Supramolecular Bidentate Ligands for Enantioselective Rh-Catalyzed Hydrogenations. Eur J Org Chem 2009, 2009, 2539. <http://dx.doi.org/10.1002/ejoc.200900158>
  • Breuil Pierre-Alain R., Reek Joost N. H.: Amino Acid Based Phosphoramidite Ligands for the Rhodium-Catalyzed Asymmetric Hydrogenation. Eur J Org Chem 2009, 2009, 6225. <http://dx.doi.org/10.1002/ejoc.200901044>
  • Moteki Shin A., Takacs James M.: Exploiting Self-Assembly for Ligand-Scaffold Optimization: Substrate-Tailored Ligands for Efficient Catalytic Asymmetric Hydroboration. Angew Chem 2008, 120, 908. <http://dx.doi.org/10.1002/ange.200703127>
  • Reetz Manfred T.: Kombinatorische Übergangsmetallkatalyse: Mischungen einzähniger Liganden zur Kontrolle der Enantio-, Diastereo- und Regioselektivität. Angew Chem 2008, 120, 2592. <http://dx.doi.org/10.1002/ange.200704327>
  • Patureau Frederic W., Kuil Mark, Sandee Albertus J., Reek Joost N. H.: METAMORPhos: Adaptive Supramolecular Ligands and Their Mechanistic Consequences for Asymmetric Hydrogenation. Angew Chem 2008, 120, 3224. <http://dx.doi.org/10.1002/ange.200705212>
  • Moteki Shin A., Takacs James M.: Exploiting Self-Assembly for Ligand-Scaffold Optimization: Substrate-Tailored Ligands for Efficient Catalytic Asymmetric Hydroboration. Angew Chem Int Ed 2008, 47, 894. <http://dx.doi.org/10.1002/anie.200703127>
  • Reetz Manfred T.: Combinatorial Transition-Metal Catalysis: Mixing Monodentate Ligands to Control Enantio-, Diastereo-, and Regioselectivity. Angew Chem Int Ed 2008, 47, 2556. <http://dx.doi.org/10.1002/anie.200704327>
  • Patureau Frederic W., Kuil Mark, Sandee Albertus J., Reek Joost N. H.: METAMORPhos: Adaptive Supramolecular Ligands and Their Mechanistic Consequences for Asymmetric Hydrogenation. Angew Chem Int Ed 2008, 47, 3180. <http://dx.doi.org/10.1002/anie.200705212>
  • Imamoto Tsuneo, Itoh Takuma, Yoshida Kazuhiro, Gridnev Ilya D.: Marked Deuterium Isotope Effects on the Enantioselectivity in Rhodium-Catalyzed Asymmetric Hydrogenation of Enamides. Chem Asian J 2008, 3, 1636. <http://dx.doi.org/10.1002/asia.200800146>
  • Goudriaan P. Elsbeth, van Leeuwen Piet W. N. M., Birkholz Mandy‐Nicole, Reek Joost N. H.: Libraries of Bidentate Phosphorus Ligands; Synthesis Strategies and Application in Catalysis. Eur J Inorg Chem 2008, 2008, 2939. <http://dx.doi.org/10.1002/ejic.200800139>
  • Chuzel Olivier, Magnier-Bouvier Caroline, Schulz Emmanuelle: Assembly of chiral monodentate ligands to chelates by donor–acceptor interactions. Tet Asymm 2008, 19, 1010. <http://dx.doi.org/10.1016/j.tetasy.2008.04.008>
  • Carbery David R.: Enamides: valuable organic substrates. Org Biomol Chem 2008, 6, 3455. <http://dx.doi.org/10.1039/b809319a>
  • Machut Cécile, Patrigeon Julien, Tilloy Sébastien, Bricout Hervé, Hapiot Frédéric, Monflier Eric: Self-Assembled Supramolecular Bidentate Ligands for Aqueous Organometallic Catalysis. Angew Chem 2007, 119, 3100. <http://dx.doi.org/10.1002/ange.200605166>
  • Machut Cécile, Patrigeon Julien, Tilloy Sébastien, Bricout Hervé, Hapiot Frédéric, Monflier Eric: Self-Assembled Supramolecular Bidentate Ligands for Aqueous Organometallic Catalysis. Angew Chem Int Ed 2007, 46, 3040. <http://dx.doi.org/10.1002/anie.200605166>
  • Slagt Vincent F., Kaiser Patrick, Berkessel Albrecht, Kuil Mark, Kluwer Alexander M., van Leeuwen Piet W. N. M., Reek Joost N. H.: Fine-Tuning Ligands for Catalysis Using Supramolecular Strategies. Eur J Inorg Chem 2007, 2007, 4653. <http://dx.doi.org/10.1002/ejic.200700550>
  • Kuil Mark, Goudriaan P. Elsbeth, Kleij Arjan W., Tooke Duncan M., Spek Anthony L., van Leeuwen Piet W. N. M., Reek Joost N. H.: Rigid bis-zinc(ii) salphen building blocks for the formation of template-assisted bidentate ligands and their application in catalysis. Dalton Trans 2007, 2311. <http://dx.doi.org/10.1039/b702375h>
  • Moteki Shin A., Wu Di, Chandra Kusum L., Reddy D. Sahadeva, Takacs James M.: TADDOL-Derived Phosphites and Phosphoramidites for Efficient Rhodium-Catalyzed Asymmetric Hydroboration. Org Lett 2006, 8, 3097. <http://dx.doi.org/10.1021/ol061117g>
  • Sandee Albertus J., Reek Joost N. H.: Bidentate ligands by supramolecular chemistry?the future for catalysis?. Dalton Trans 2006, 3385. <http://dx.doi.org/10.1039/b606045p>