A convergent rhodium-catalysed asymmetric synthesis of tetrahydroquinolines.

Rh-catalysed conjugate additions of 2-aminophenyl boronic acid derivatives were exploited in diastereoselective and asymmetric syntheses of tetrahydroquinolines. In both cases, combinatorial variation of the substitution of the tetrahydroquinoline ring system was possible.

• Publication year

  2014

• Venue

  Chemical Communications

• Publication date

  2014-08-07

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1039/c4cc04940cPMID 25052422
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Enantioselective synthesis of hexahydrofuro[3,2-c] quinolines through a multicatalytic and multicomponent process. A new “aromatic sandwich” model for BINOL-phosphoric acid catalyzed reactions

  2014cited by this paper
• A highly diastereo- and enantioselective synthesis of tetrahydroquinolines: quaternary stereogenic center inversion and functionalization.

  2013cited by this paper
• Conjugate-base-stabilized Brønsted acids as asymmetric catalysts: enantioselective Povarov reactions with secondary aromatic amines.

  2013cited by this paper
• Highly enantioselective transfer hydrogenation of quinolines catalyzed by gold phosphates: achiral ligand tuning and chiral-anion control of stereoselectivity.

  2012cited by this paper
• Rhodium and copper-catalyzed asymmetric conjugate addition of alkenyl nucleophiles.

  2012cited by this paper
• Dihydrophenanthridine: a new and easily regenerable NAD(P)H model for biomimetic asymmetric hydrogenation.

  2012cited by this paper
• Direct enantioselective access to 4-substituted tetrahydroquinolines by catalytic asymmetric transfer hydrogenation of quinolines.

  2011cited by this paper
• Highly enantioselective hydrogenation of quinolines using phosphine-free chiral cationic ruthenium catalysts: scope, mechanism, and origin of enantioselectivity.

  2011cited by this paper
• Selective activation of enantiotopic C(sp3)-hydrogen by means of chiral phosphoric acid: asymmetric synthesis of tetrahydroquinoline derivatives.

  2011cited by this paper
• Chiral phosphoric acid-catalyzed enantioselective three-component Povarov reaction using enecarbamates as dienophiles: highly diastereo- and enantioselective synthesis of substituted 4-aminotetrahydroquinolines.

  2011cited by this paper
• Catalyst control in sequential asymmetric allylic substitution: stereodivergent access to N,N-diprotected unnatural amino acids.

  2011cited by this paper
• Bull. Chem. Soc. Jpn. への投稿のすすめ

  2011cited by this paper
• Enantioselective organocatalytic C-H bond functionalization via tandem 1,5-hydride transfer/ring closure: asymmetric synthesis of tetrahydroquinolines.

  2010cited by this paper
• Efficient entry into 2-substituted tetrahydroquinoline systems through alkylative ring expansion: stereoselective formal synthesis of (+/-)-martinellic acid.

  2010cited by this paper
• Synthetic applications of rhodium catalysed conjugate addition.

  2010cited by this paper
• Asymmetric Cooperative Catalysis of Strong Brønsted Acid–Promoted Reactions Using Chiral Ureas

  2010cited by this paper
• Iridium‐Catalyzed Asymmetric Allylic Amination with Polar Amines: Access to Building Blocks with Lead‐Like Molecular Properties

  2010cited by this paper
• Asymmetric Brønsted acid catalysis in aqueous solution

  2010cited by this paper
• Organocatalytic asymmetric Povarov reactions with 2- and 3-vinylindoles.

  2010cited by this paper
• Asymmetric three-component inverse electron-demand aza-Diels-Alder reaction: efficient synthesis of ring-fused tetrahydroquinolines.

  2010cited by this paper
• Efficient process intensification of fine chemical production: a new classification tool for flow chemistry technologies

  2010cited by this paper
• Consecutive intramolecular hydroamination/asymmetric transfer hydrogenation under relay catalysis of an achiral gold complex/chiral Brønsted acid binary system.

  2009cited by this paper
• Chiral Brønsted acid-catalyzed enantioselective three-component Povarov reaction.

  2009cited by this paper
• pH-regulated asymmetric transfer hydrogenation of quinolines in water.

  2009cited by this paper
• Catalytic enantioselective intramolecular redox reactions: ring-fused tetrahydroquinolines.

  2009cited by this paper
• Convergent synthesis of dihydroquinolones from o-aminoarylboronates

  2009cited by this paper
• Convergent, regiospecific synthesis of quinolines from o-aminophenylboronates.

  2008cited by this paper
• Hydrogenation of quinolines using a recyclable phosphine-free chiral cationic ruthenium catalyst: enhancement of catalyst stability and selectivity in an ionic liquid.

  2008cited by this paper
• The development of double axially chiral phosphoric acids and their catalytic transfer hydrogenation of quinolines.

  2008cited by this paper
• Asymmetric Counterion Pair Catalysis: An Enantioselective Brønsted Acid‐Catalyzed Protonation

  2008cited by this paper
• Asymmetric hydrogenation of quinolines with high substrate/catalyst ratio.

  2007cited by this paper
• Highly selective rhodium-catalyzed conjugate addition reactions of 4-oxobutenamides.

  2007cited by this paper
• A highly enantioselective Brønsted acid catalyzed cascade reaction: organocatalytic transfer hydrogenation of quinolines and their application in the synthesis of alkaloids.

  2006cited by this paper
• Chiral Brønsted acid-catalyzed inverse electron-demand aza Diels-Alder reaction.

  2006cited by this paper
• Asymmetric hydrogenation of quinolines catalyzed by iridium complexes of BINOL-derived diphosphonites.

  2006cited by this paper
• Practical P‐Chiral Phosphane Ligand for Rh‐Catalyzed Asymmetric Hydrogenation

  2005cited by this paper
• Determination of absolute configuration via vibrational circular dichroism.

  2004cited by this paper
• Computational medicinal chemistry for drug discovery

  2003cited by this paper
• Highly enantioselective iridium-catalyzed hydrogenation of heteroaromatic compounds, quinolines.

  2003cited by this paper
• Rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds.

  2003cited by this paper
• Rhodium-catalyzed asymmetric 1,4-addition and its related asymmetric reactions.

  2003cited by this paper
• Rhodium-Catalyzed Asymmetric 1,4-Addition of Organoboronic Acids and Their Derivatives to Electron Deficient Olefins

  2001cited by this paper
• Palladium-catalyzed borylation of ortho-substituted phenyl halides and application to the one-pot synthesis of 2,2'-disubstituted biphenyls.

  2000cited by this paper
• Rhodium-Catalyzed Asymmetric 1,4-Addition of Aryl- and Alkenylboronic Acids to Enones

  1998cited by this paper
• Rhodium-Catalyzed Conjugate Addition of Aryl- or 1-Alkenylboronic Acids to Enones

  1997cited by this paper
• Catalytic asymmetric aza Diels-Alder reactions using a chiral lanthanide Lewis acid. Enantioselective synthesis of tetrahydroquinoline derivatives using a catalytic amount of a chiral source

  1996cited by this paper
• Recent progress in the synthesis of 1,2,3,4,-tetrahydroquinolines

  1996cited by this paper
• Strategies and Tactics in Organic Synthesis

  1993cited by this paper
• Argatroban, A Selective, Potent Thrombin Inhibitor

  1991cited by this paper
• Rhodium catalyzed hydrogenation of quinolines and isoquinolines under water-gas shift conditions.

  1989cited by this paper
• Dynemicin A, a novel antibiotic with the anthraquinone and 1,5-diyn-3-ene subunit.

  1989cited by this paper
• Vicinal Proton Coupling in Nuclear Magnetic Resonance

  1963cited by this paper

• Enantiodivergent kinetic resolution of 4-substituted 1,2,3,4-tetrahydroquinolines employing amine oxidase.

  2024cites this paper
• Catalytic asymmetric indolization by a desymmetrizing [3 + 2] annulation strategy

  2023cites this paper
• HFIP-Empowered One-Pot Synthesis of C4-Aryl-Substituted Tetrahydroquinolines with Propargylic Chlorides and Anilines.

  2023cites this paper
• Ball-milling Synthesis of Tetrahydroquinolines via ‘One-pot’ Three-component Diels-Alder Reaction Catalyzed by Phosphotungstic Acid

  2020cites this paper
• Cobalt-Catalyzed Enantioselective Hydroboration/Cyclization of 1,7-Enynes: Asymmetric Synthesis of Chiral Quinolinones Containing Quaternary Stereogenic Centers.

  2019cites this paper
• Progress in the Chemistry of Tetrahydroquinolines.

  2019cites this paper
• Bis(norbornadiene)rhodium(I) Tetrafluoroborate

  2019cites this paper
• Intermolecular Dehydrative [4 + 2] Aza-Annulation of N-Arylamides with Alkenes: A Direct and Divergent Entrance to Aza-Heterocycles.

  2019cites this paper
• Synergistic Chemo/Biocatalytic Synthesis of Alkaloidal Tetrahydroquinolines

  2018cites this paper
• Transformation of N, N-Dimethylaniline N-Oxides into Diverse Tetrahydroquinoline Scaffolds via Formal Povarov Reactions.

  2018cites this paper
• Metal‐Free One‐Pot Synthesis of (Tetrahydro)Quinolines through Three‐Component Assembly of Arenediazonium Salts, Nitriles, and Styrenes

  2018cites this paper
• Recent advances in rhodium-catalyzed asymmetric synthesis of heterocycles.

  2017cites this paper
• An Efficient One-Pot Three-Component Synthesis of Some New Polyhydroquinolines via Enaminone Intermediates

  2017cites this paper
• Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines

  2016cites this paper
• Palladium-Catalyzed Cascade sp2 C–H Bond Functionalizations Allowing One-Pot Access to 4-Aryl-1,2,3,4-tetrahydroquinolines from N-Allyl-N-arylsulfonamides

  2016cites this paper
• Synthetic approaches to 4-(het)aryl-3,4-dihydroquinolin-2(1H)-ones

  2016cites this paper
• Homogeneous rhodium(i)-catalysis in de novo heterocycle syntheses.

  2016cites this paper
• A Convergent Rhodium-Catalyzed Asymmetric Synthesis of Tetrahydroquinolines.

  2015cites this paper
• Chiral gold phosphate catalyzed tandem hydroamination/asymmetric transfer hydrogenation enables access to chiral tetrahydroquinolines.

  2015cites this paper
• Highly Enantioselective SPINOL‐Derived Phosphoric Acid Catalyzed Transfer Hydrogenation of Diverse C=N‐Containing Heterocycles

  2015cites this paper