Highly Enantioselective [3+2] Annulation of Indoles with Quinones to Access Structurally Diverse Benzofuroindolines.

No abstract is available for this paper.

• Publication year

  2018

• Venue

  Angewandte Chemie

• Publication date

  2018-03-26

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1002/anie.201800733PMID 29405544
• 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.

• Copper Catalyzed Asymmetric [4 + 2] Annulations of D-A Cyclobutanes with Aldehydes

  2018cited by this paper
• SaBOX/Copper Catalysts for Highly Syndio-Specific Atom Transfer Radical Polymerization of Methyl Methacrylate

  2017cited by this paper
• Unified biomimetic assembly of voacalgine A and bipleiophylline via divergent oxidative couplings.

  2017cited by this paper
• One-step formation of dihydrofuranoindoline cores promoted by a hypervalent iodine reagent.

  2017cited by this paper
• Access to Hexahydrocarbazoles: The Thorpe-Ingold Effects of the Ligand on Enantioselectivity.

  2017cited by this paper
• Bifunctional Photocatalysts for Enantioselective Aerobic Oxidation of β-Ketoesters.

  2017cited by this paper
• External oxidant-free electrooxidative [3 + 2] annulation between phenol and indole derivatives

  2017cited by this paper
• Reaction of Donor-Acceptor Cyclobutanes with Indoles: A General Protocol for the Formal Total Synthesis of (±)-Strychnine and the Total Synthesis of (±)-Akuammicine.

  2017cited by this paper
• Cy-SaBOX/Copper(II)-Catalyzed Highly Diastereo- and Enantioselective Synthesis of Bicyclic N,O Acetals.

  2016cited by this paper
• Enantioselective Oxetane Ring Opening with Chloride: Unusual Use of Wet Molecular Sieves for the Controlled Release of HCl.

  2016cited by this paper
• Dearomatization through Halofunctionalization Reactions.

  2016cited by this paper
• [3 + 2]-Annulations of N-alkyl-3-substituted indoles with quinone monoketals catalysed by Brønsted acids.

  2016cited by this paper
• Electrolytic macrocyclizations: scalable synthesis of a diazonamide-based drug development candidate.

  2015cited by this paper
• Asymmetric H2O-Nucleophilic Ring Opening of D-A Cyclopropanes: Catalyst Serves as a Source of Water.

  2015cited by this paper
• Lewis Acid Catalyzed [3+2] Coupling of Indoles with Quinone Monoacetals or Quinone Imine Ketal

  2014cited by this paper
• Transition-metal-catalyzed asymmetric allylic dearomatization reactions.

  2014cited by this paper
• Side arm strategy for catalyst design: modifying bisoxazolines for remote control of enantioselection and related.

  2014cited by this paper
• Direct oxidative coupling of N-acetyl indoles and phenols for the synthesis of benzofuroindolines related to phalarine.

  2014cited by this paper
• A sidearm-assisted phosphine for catalytic ylide intramolecular cyclopropanation

  2014cited by this paper
• Highly enantioselective [3+2] coupling of indoles with quinone monoimines promoted by a chiral phosphoric acid.

  2014cited by this paper
• Bioinspired direct access to benzofuroindolines by oxidative [3 + 2] annulation of phenols and indoles.

  2014cited by this paper
• Synthetic Routes Towards Benzofuro[2,3-b]pyrroles and Benzofuro[2,3-b]indoles

  2014cited by this paper
• Biomimetic synthesis of ent-(-)-azonazine and stereochemical reassignment of natural product.

  2013cited by this paper
• Recent developments in the catalytic, asymmetric construction of pyrroloindolines bearing all-carbon quaternary stereocenters.

  2013cited by this paper
• Voacalgines A–E, new indole alkaloids from Voacanga grandifolia

  2013cited by this paper
• Unraveling the Numerous Biosynthetic Products of the Marine Sediment-Derived Fungus, Aspergillus insulicola.

  2012cited by this paper
• Katalytische asymmetrische Desaromatisierungen

  2012cited by this paper
• Catalytic asymmetric dearomatization reactions.

  2012cited by this paper
• FeCl3-mediated Friedel-Crafts hydroarylation with electrophilic N-acetyl indoles for the synthesis of benzofuroindolines.

  2012cited by this paper
• Lewis acid-catalyzed Friedel-Crafts alkylations of 3-hydroxy-2-oxindole: an efficient approach to the core structure of azonazine.

  2012cited by this paper
• An enantioselective synthesis of 2-aryl cycloalkanones by Sc-catalyzed carbon insertion.

  2011cited by this paper
• A Second‐Generation Formal Synthesis of (+)‐Haplophytine

  2011cited by this paper
• Total synthesis of diazonamide A.

  2011cited by this paper
• Organocatalyzed enantioselective fluorocyclizations.

  2011cited by this paper
• Azonazine, a novel dipeptide from a Hawaiian marine sediment-derived fungus, Aspergillus insulicola.

  2010cited by this paper
• The importance of 1:1 and 1:2 metal–ligand species in chiral copper(II)–bis(oxazoline) complexes for catalytic activity

  2010cited by this paper
• A concise formal synthesis of diazonamide A by the stereoselective construction of the C10 quaternary center.

  2010cited by this paper
• Synthesis and preliminary biological studies of 3-substituted indoles accessed by a palladium-catalyzed enantioselective alkene difunctionalization reaction.

  2010cited by this paper
• Combining Fluorous and Triazole Moieties for the Tagging of Chiral Azabis(oxazoline) Ligands

  2009cited by this paper
• Total synthesis of (+)-haplophytine.

  2009cited by this paper
• Total synthesis of (+)-haplophytine.

  2009cited by this paper
• Dependence of enantioselectivity on the ligand/metal ratio in the asymmetric Michael addition of indole to benzylidene malonates: electronic influence of substrates.

  2008cited by this paper
• Bipleiophylline, an unprecedented cytotoxic bisindole alkaloid constituted from the bridging of two indole moieties by an aromatic spacer unit.

  2008cited by this paper
• The synthetic challenge of diazonamide A, a macrocyclic indole bis-oxazole marine natural product.

  2008cited by this paper
• Diazonamides C–E, new cytotoxic metabolites from the ascidian Diazona sp.

  2008cited by this paper
• An expedient formal total synthesis of (-)-diazonamide A via a powerful, stereoselective O-aryl to C-aryl migration to form the C10 quaternary center.

  2007cited by this paper
• Therapeutic anticancer efficacy of a synthetic diazonamide analog in the absence of overt toxicity

  2007cited by this paper
• Using a tripod as a chiral chelating ligand: chemical exchange between equivalent molecular structures in palladium catalysis with 1,1,1-tris(oxazolinyl)ethane ("trisox").

  2007cited by this paper
• Diazonamide toxins reveal an unexpected function for ornithine δ-amino transferase in mitotic cell division

  2007cited by this paper
• Stereochemical consequences of threefold symmetry in asymmetric catalysis: distorting C3 Chiral 1,1,1-tris(oxazolinyl)ethanes ("trisox") in CuII Lewis acid catalysts.

  2007cited by this paper
• Construction of the "left domain" of haplophytine.

  2007cited by this paper
• Studies toward the total synthesis of phalarine: a survey of some biomimetic possibilities

  2006cited by this paper
• Highly enantioselective michael additions of indole to benzylidene malonate using simple bis(oxazoline) ligands: importance of metal/ligand ratio.

  2006cited by this paper
• Bisoxazolines with one and two sidearms: stereodirecting ligands for copper-catalysed asymmetric allylic oxidations of alkenes.

  2006cited by this paper
• Enantioselective organocatalytic construction of pyrroloindolines by a cascade addition-cyclization strategy: synthesis of (-)-flustramine B.

  2004cited by this paper
• Diazonamide A and a synthetic structural analog: disruptive effects on mitosis and cellular microtubules and analysis of their interactions with tubulin.

  2003cited by this paper
• A concise and flexible total synthesis of (-)-diazonamide A.

  2003cited by this paper
• The second total synthesis of diazonamide A.

  2003cited by this paper
• Total synthesis of diazonamide A.

  2002cited by this paper
• Sidearm effect: improvement of the enantiomeric excess in the asymmetric Michael addition of indoles to alkylidene malonates.

  2002cited by this paper
• Total Synthesis of Nominal Diazonamides—Part 2: On the True Structure and Origin of Natural Isolates

  2001cited by this paper
• PhosphinooxazolinesA New Class of Versatile, Modular P,N-Ligands for Asymmetric Catalysis

  2000cited by this paper
• Phosphinooxazolines--a new class of versatile, modular P,N-ligands for asymmetric catalysis.

  2000cited by this paper
• An Improved Procedure for the Preparation of 2,2-Bis[2-[4(S)- tert-butyl-1,3-oxazolinyl]]propane [(S,S)-tert-Butylbis(oxazoline)] and Derived Copper(II) Complexes

  1998cited by this paper
• Chirale C2‐symmetrische CuII‐Komplexe als Katalysatoren für enantioselektive Hetero‐Diels‐Alder‐Reaktionen

  1998cited by this paper
• Chiral C2 -Symmetric CuII Complexes as Catalysts for Enantioselective Hetero-Diels-Alder Reactions.

  1998cited by this paper
• Design, Synthesis, and Evaluation of Small-Molecule Libraries

  1996cited by this paper
• Synthesis and Applications of Small Molecule Libraries.

  1996cited by this paper
• Isolation and structure determination of diazonamides A and B, unusual cytotoxic metabolites from the marine ascidian Diazona chinensis

  1991cited by this paper
• Synthesis and mass spectral studies of fluorine containing 5a, 7b, 12a, 14b-tetrahydrobisindolo [2,3-b:2′,3′-b′] benzo [1,2-d:4,5-d′] difurans

  1988cited by this paper
• Metabolic Products of Aspregillus terreus. VI. Metabolites of the Strain IFO 8835. (3). The Isolation and Chemical Structures of Colorless Metabolites

  1981cited by this paper
• Structural analysis by 13C NMR spectroscopy of pleiocorine, a new bisindole alkaloid from , alstonia deplanchei van heurck et muell. arg.

  1974cited by this paper
• The Cycloaddition Reaction of 3-Alkylindoles with p-Benzoquinone

  1966cited by this paper

• Palladium‐Catalyzed Asymmetric [3+2] Cyclization for the Synthesis of Chiral 2,3‐dihydrofuran Regulated by the Side‐Arm Effect of diSaBOX Ligands

  2026cites this paper
• Organocatalytic Atroposelective Arylation: A Practical Strategy for the Synthesis of Axially Chiral Compounds

  2026cites this paper
• Enantioselective Preparation of (N,O)-, (N,N)- and (N,S)-Spiroketal Moieties

  2025cites this paper
• Recent Advances in the Multifunctionalization Reactions of Indoles

  2025cites this paper
• Atroposelective Synthesis of Isoxazole‐Derived Amino Alcohols via Organocatalytic Arylation Reaction

  2025cites this paper
• Catalyst-Free [3 + 2] Cycloaddition of Benzimidazole Esters and Quinone Esters: Divergent Synthesis of N-Heterocycles.

  2025cites this paper
• Acid-Enabled Dearomative Umpolung of 3-Indolylquinones toward C3-Oxygenated Benzofuro[2,3-b]indolines.

  2025cites this paper
• Versatile Biaryls and Fused Aromatics through Oxidative Coupling of Hydroquinones with (Hetero)Arenes

  2024cites this paper
• Iron‐Catalyzed, Visible‐Light‐Mediated Decarboxylative Cyclization Reactions: A Viable Approach to 2,3‐Dihydrobenzofuran Derivatives

  2024cites this paper
• De novo synthesis of atropisomeric benzofurans via Cu/SPDO complex catalyzed asymmetric formal [3 + 2] annulation

  2024cites this paper
• Copper Catalyzed [3 + 2] Annulation Reaction of Exocyclic Sulfonyl Enamides for the Synthesis of N,O-Spiroketal and Spiroketal.

  2024cites this paper
• Switchable divergent synthesis of chiral indole derivatives via catalytic asymmetric dearomatization of 2,3-disubstituted indoles

  2024cites this paper
• Pd/NBE-Mediated Annulation of Aryl Triflates with Oxiranes: Efficient Synthesis of 2,3-Dihydrobenzofurans

  2024cites this paper
• Chiral Phosphoric Acid‐Catalyzed Enantioselective Synthesis of Axially Chiral Compounds Involving Indole Derivatives

  2023cites this paper
• Pd-Catalyzed Intramolecular Dearomative [4 + 2] Cycloaddition of Naphthalenes with Arylalkynes.

  2023cites this paper
• Sc(OTf)3-Catalyzed Domino C-C/C-N Bond Formation of Aziridines with Quinones via Radical Pathway.

  2023cites this paper
• Diversity‐Oriented Catalytic Asymmetric Dearomatization of Indoles with o‐Quinone Diimides

  2023cites this paper
• Enantioselective Synthesis of 2,3,3a,8a-Tetrahydrofuro[2,3-b]benzofuran Scaffolds Enabled by Cu(II)/SPDO-Catalyzed [3+2] Cycloaddition of 2,3-Dihydrofuran and Quinone Esters.

  2023cites this paper
• Organocatalytic asymmetric [2 + 2] cycloaddition of alkynes with quinones

  2023cites this paper
• Catalytic Asymmetric [3 + 2] Cycloaddition of Exocyclic Enol Ethers for the Synthesis of Spiroketals

  2023cites this paper
• Enantioselective Synthesis of cis-Decalins by Merging the Birch Reduction and Inverse-Electron-Demand Diels-Alder Reaction.

  2023cites this paper
• Cascade asymmetric dearomative cyclization reactions via transition-metal-catalysis

  2022cites this paper
• Side arm modified chiral bisoxazoline ligands: Recent development and prospect in asymmetric catalysis

  2022cites this paper
• Efficient synthesis of spiro diheterocycles via multi-component dicyclization reaction.

  2022cites this paper
• Recent Advances on the Construction of Chiral Dihydrobenzofurans by Asymmetric [3+2] Cyclization Reactions of Phenols (Quinones) and Alkenes

  2022cites this paper
• Rapid Construction of Enantioenriched Benzofurochromanes by SaBOX/Copper(II) Catalyzed Enantioselective [3 + 2] Annulation of γ-Chromenes with Quinones.

  2022cites this paper
• Reactivity Modulation of Labile Quinones and Biomimetic Catalytic Transformations

  2022cites this paper
• Chemo-, regio- and enantioselective dearomative (3+2) reaction of non-functionalized 1-naphthols

  2022cites this paper
• Sc(OTf)3-Catalyzed Formal [3 + 3] Cycloaddition Reaction of Diaziridines and Quinones for the Synthesis of Benzo[e][1,3,4]oxadiazines.

  2021cites this paper
• Silica gel-promoted synthesis of multisubstituted spiroindolenines from tryptamines and γ-chloro-α,β-unsaturated ketones

  2021cites this paper
• Catalytic asymmetric preparation of pyrroloindolines: strategies and applications to total synthesis.

  2021cites this paper
• Ni-Catalyzed asymmetric hetero-Diels–Alder reactions of conjugated vinyl azides: synthesis of chiral azido polycycles

  2021cites this paper
• Polycyclic heterocycles by condensation of 1,4-benzoquinone analogs and nucleophiles

  2021cites this paper
• Highly Regio- and Stereoselective Cascade of β,γ-Unsaturated Ketones by Dipeptided Phosphonium Salt Catalysis: Stereospecific Construction of Dihydrofuro-Fused [2,3-b] Skeletons.

  2021cites this paper
• Enantioselective synthesis of C3 substituted benzofuroindolines via catalytic asymmetric [3 + 2] cyclization of 3-substituted indoles with p-benzoquinones

  2021cites this paper
• Enantioselective Dearomative [3+2] Annulation of 3‐Hydroxymaleimides with Azonaphthalenes

  2021cites this paper
• Copper-Catalyzed Asymmetric Diyne Cyclization via [1,2]-Stevens-Type Rearrangement for the Synthesis of Chiral Chromeno[3,4-c]pyrroles.

  2021cites this paper
• Enantioselective Synthesis of Axially Chiral Biaryls by Diels-Alder/Retro-Diels-Alder Reaction of 2-Pyrones with Alkynes.

  2021cites this paper
• Recent Advances in Synthetic Strategies to 2,3-Dihydrobenzofurans

  2020cites this paper
• Harnessing structurally unbiased ortho-benzoquinone monoimine for biomimetic oxidative [4+2] cycloaddition with enamines.

  2020cites this paper
• Expedient Synthesis of Dihydroisoquinolines by Cascade Annulation of Nitrovinylbenzoquinone

  2020cites this paper
• Atroposelective Synthesis of Axially Chiral 3-Arylindoles by Copper-Catalyzed Asymmetric Cross-Coupling of Indoles with Quinones and Naphthoquinones.

  2020cites this paper
• A Versatile Enantioselective Catalytic Cyclopropanation-Rearrangement Approach to the Divergent Construction of Chiral Spiroaminals and Fused Bicyclic Acetals.

  2020cites this paper
• Hemin-Catalyzed Oxidative Phenol-Hydrazone [3+3] Cycloaddition Enables Rapid Construction of 1,3,4-Oxadiazines.

  2020cites this paper
• Construction of Unusual Indole-Based Heterocycles from Tetrahydro-1H-pyridazino[3,4-b]indoles

  2020cites this paper
• Formal oxo- and aza-[3 + 2] reactions of α-enaminones and quinones: a double divergent process and the roles of chiral phosphoric acid and molecular sieves

  2020cites this paper
• Coinage Metal (Bisfluorosulfonyl)imide Complexes: Preparation, Characterization, and Catalytic Applications

  2020cites this paper
• Synthesis of chiral [2,3]-fused indolines through enantioselective dearomatization inverse-electron-demand Diels-Alder reaction/oxidation of indoles with 2-(2-nitrovinyl)-1,4-benzoquinone.

  2020cites this paper
• Five-Membered Ring Systems: With O & N Atoms

  2020cites this paper
• Asymmetric Epoxidation of α,β‐Unsaturated Ketones Catalyzed by Chiral Iron Complexes of (R,R)‐3,4‐Diaminopyrrolidine Derived N4‐Ligands with Camphorsulfonyl Sidearms

  2020cites this paper
• Hemin-catalyzed biomimetic oxidative phenol-indole [3 + 2] reactions in aqueous media.

  2019cites this paper
• Asymmetric Dearomatization of Indole Derivatives with N-Hydroxycarbamates Enabled by Photoredox Catalysis.

  2019cites this paper
• Asymmetric Ring-Opening of Donor–Acceptor Cyclopropanes with Primary Arylamines Catalyzed by a Chiral Heterobimetallic Catalyst

  2019cites this paper
• CuH-Catalyzed Synthesis of 3-Hydroxyindolines and 2-Aryl-3H-indol-3-ones from o-Alkynylnitroarenes, Using Nitro as Both the Nitrogen and Oxygen Source.

  2019cites this paper
• Enantioselective Oxidative Phenol-Indole [3 + 2] Coupling Enabled by Biomimetic Mn(III)/Brønsted Acid Relay Catalysis

  2019cites this paper
• Atroposelective Construction of Arylindoles by Chiral Phosphoric Acid-Catalyzed Cross-Coupling of Indoles and Quinones.

  2019cites this paper
• Divergent synthesis of chiral cyclic azides via asymmetric cycloaddition reactions of vinyl azides

  2019cites this paper
• Phosphine-catalyzed dearomative [3+2] annulation of 3-nitroindoles and allenoates

  2019cites this paper
• Access to Polycyclic Sulfonyl Indolines via Fe(II)-Catalyzed or UV-Driven Formal [2 + 2 + 1] Cyclization Reactions of N-((1H-indol-3-yl)methyl)propiolamides with NaHSO3.

  2019cites this paper
• A Synthesis of Multifunctionalized Indoles from [3 + 2] Annulation of 2-Bromocyclopropenes with Anilines.

  2019cites this paper
• Synthesis of poly-functionalized benzofurans via one-pot domino oxidation/[3+2] cyclization reactions of a hydroquinone ester and ynamides

  2019cites this paper
• Unprecedented Tandem Conjugate Addition/C‐O Ester Migration ofα‐Cyano Arylacetates with a Quinone Monoimine

  2019cites this paper
• Synthesis of Novel Pterocarpen Analogues via [3 + 2] Coupling‐Elimination Cascade of α,α‐Dicyanoolefins with Quinone Monoimines

  2019cites this paper
• Recent advances in indoline synthesis

  2019cites this paper
• Revisiting Furodiindolines: One-Pot Synthesis of Furodiindolines Using Indole 2,3-Epoxide Surrogates and Their Synthetic Applications.

  2019cites this paper
• Catalyst-Controlled Chemoselective All-Alkene [2 + 2 + 2] and [2 + 2] Cyclizations of Enamides with Electron-Deficient Alkenes.

  2019cites this paper
• A catalytic asymmetric one-pot [3+2] cyclization/semipinacol rearrangement sequence: an efficient construction of a multi-substituted 3H-spiro[benzofuran-2,1'-cyclopentane] skeleton.

  2019cites this paper
• Selectivity Switch in a Rhodium(II) Carbene Triggered Cyclopentannulation: Divergent Access to Three Polycyclic Indolines.

  2019cites this paper
• Eight-Step Total Synthesis of Phalarine by Bioinspired Oxidative Coupling of Indole and Phenol.

  2019cites this paper
• Catalytic Asymmetric Dearomative [3+2] Cyclisation of 1,4‐Quinone with 2,3‐Disubstituted Indoles

  2019cites this paper
• Highly Enantioselective Nickel-Catalyzed Oxa-[3+3]-annulation of Phenols with Benzylidene Pyruvates for Chiral Chromans.

  2018cites this paper
• Enantioselective [3 + 2] Formal Cycloaddition of 1-Styrylnaphthols with Quinones Catalyzed by a Chiral Phosphoric Acid.

  2018cites this paper
• Rhodium(III)-Catalyzed Redox-Neutral C-H Activation/Annulation of N-Aryloxyacetamides with Alkynyloxiranes: Synthesis of Highly Functionalized 2,3-Dihydrobenzofurans.

  2018cites this paper
• Copper-Catalyzed Enantioselective Synthesis of Benzofuroindolines

  2018cites this paper
• Yb(NTf2)3/HFIP induced high isotacticity in atom transfer radical polymerization of methyl methacrylate

  2018cites this paper
• Sidearm Modified Bisoxazoline Ligands and Their Applications

  2018cites this paper
• Recent Developments in Transition Metal‐Catalyzed Dearomative Cyclizations of Indoles as Dipolarophiles for the Construction of Indolines

  2018cites this paper
• Side arm modi fi ed chiral bisoxazoline ligands: Recent development and prospect in asymmetric catalysis

  year unknowncites this paper