Chiral Phosphoric Acid Catalyzed Intramolecular Dearomative Michael Addition of Indoles to Enones.

No abstract is available for this paper.

• Publication year

  2017

• Venue

  Organic Letters

• Publication date

  2017-02-01

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/acs.orglett.6b03610PMID 28145710
• 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.

• Highly efficient synthesis and stereoselective migration reactions of chiral five-membered aza-spiroindolenines: scope and mechanistic understanding

  2016cited by this paper
• The Organocatalytic Approach to Enantiopure 2H- and 3H-Pyrroles: Inhibitors of the Hedgehog Signaling Pathway.

  2016cited by this paper
• Synthesis of Spirocyclic Indolenines.

  2016cited by this paper
• Enantioselective Construction of Spiroindolines with Three Contiguous Stereogenic Centers and Chiral Tryptamine Derivatives via Reactive Spiroindolenine Intermediates.

  2015cited by this paper
• Catalytic asymmetric dearomatizing redox cross coupling of ketones with aryl hydrazines giving 1,4-diketones.

  2015cited by this paper
• Copper-catalyzed intermolecular asymmetric propargylic dearomatization of indoles.

  2015cited by this paper
• Silver(I)- or copper(II)-mediated dearomatization of aromatic ynones: direct access to spirocyclic scaffolds.

  2015cited by this paper
• Strategies for the asymmetric functionalization of indoles: an update.

  2015cited by this paper
• Advances in Dearomatization Strategies of Indoles

  2015cited by this paper
• Synthesis of 3-arylated indolines from dearomatization of indoles

  2015cited by this paper
• Asymmetric dearomatization of indoles through a Michael/Friedel-Crafts-type cascade to construct polycyclic spiroindolines.

  2015cited by this paper
• Enantioselective Arylative Dearomatization of Indoles via Pd-Catalyzed Intramolecular Reductive Heck Reactions.

  2015cited by this paper
• Thiourea‐Catalyzed Addition of Indoles to Aliphatic β,γ‐Unsaturated α‐Ketoesters

  2015cited by this paper
• Dearomatization of tryptophols via a vanadium-catalyzed asymmetric epoxidation and ring-opening cascade.

  2014cited by this paper
• Organocatalytic asymmetric arylative dearomatization of 2,3-disubstituted indoles enabled by tandem reactions.

  2014cited by this paper
• Chiral‐Amine‐Catalyzed Asymmetric Bromocyclization of Tryptamine Derivatives

  2014cited by this paper
• Ir-catalyzed intermolecular asymmetric allylic dearomatization reaction of indoles

  2014cited by this paper
• 手性磷酸催化的C（3）-取代吲哚和甲基乙烯基酮不对称串联反应

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

  2014cited by this paper
• Recent advances in dearomatization of heteroaromatic compounds.

  2014cited by this paper
• Pd(0)-catalyzed alkenylation and allylic dearomatization reactions between nucleophile-bearing indoles and propargyl carbonate.

  2014cited by this paper
• Metal-free enantioselective electrophilic activation of allenamides: stereoselective dearomatization of indoles.

  2014cited by this paper
• Rapid Access to Spirocyclized Indolenines via Palladium-Catalyzed Cascade Reactions of Tryptamine Derivatives and Propargyl Carbonate

  2014cited by this paper
• Catalytic asymmetric synthesis of [2,3]-fused indoline heterocycles through inverse-electron-demand aza-Diels-Alder reaction of indoles with azoalkenes.

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

  2014cited by this paper
• Catalytic Enantioconvergent Decarb­oxylative Allylic Alkylation of Allyl Indol­enin‐3‐carboxylates

  2013cited by this paper
• N-indolyltriethylborate: a useful reagent for synthesis of C3-quaternary indolenines.

  2013cited by this paper
• Enantioselective cyclization of enamide-ynes and application to the synthesis of the kopsifoline core.

  2013cited by this paper
• Palladium-catalyzed decarboxylative allylation and benzylation of N-alloc and N-Cbz indoles.

  2013cited by this paper
• A combined theoretical and experimental investigation into the highly stereoselective migration of spiroindolenines.

  2013cited by this paper
• Highly enantioselective bromocyclization of tryptamines and its application in the synthesis of (-)-chimonanthine.

  2013cited by this paper
• Ruthenium-catalyzed intramolecular allylic dearomatization reaction of indole derivatives.

  2013cited by this paper
• Palladium catalyzed decarboxylative rearrangement of N-alloc indoles.

  2013cited by this paper
• Ru-catalyzed intermolecular dearomatization reaction of indoles with allylic alcohols

  2013cited by this paper
• Diversity oriented synthesis of indole-based peri-annulated compounds via allylic alkylation reactions

  2013cited by this paper
• Enantioselective functionalization of indoles and pyrroles via an in situ-formed spiro intermediate.

  2013cited by this paper
• Copper-catalyzed highly enantioselective cyclopentannulation of indoles with donor-acceptor cyclopropanes.

  2013cited by this paper
• Pd-catalyzed asymmetric allylic alkylations of 3-substituted indoles using chiral P/olefin ligands.

  2013cited by this paper
• Enantioselective gold-catalyzed synthesis of polycyclic indolines.

  2012cited by this paper
• Palladium(0)-catalyzed dearomative arylation of indoles: convenient access to spiroindolenine derivatives.

  2012cited by this paper
• Palladium-catalyzed C3-benzylation of indoles.

  2012cited by this paper
• Enantioselective copper-catalyzed construction of aryl pyrroloindolines via an arylation-cyclization cascade.

  2012cited by this paper
• Enantioselective construction of pyrroloindolines via chiral phosphoric acid catalyzed cascade Michael addition-cyclization of tryptamines.

  2012cited by this paper
• Organocatalyzed enantioselective formal [4 + 2] cycloaddition of 2,3-disubstituted indole and methyl vinyl ketone.

  2012cited by this paper
• Catalytic asymmetric dearomatization reactions.

  2012cited by this paper
• Exploiting the electrophilic properties of indole intermediates: new options in designing asymmetric reactions.

  2012cited by this paper
• Enantioselective synthesis of spiro cyclopentane-1,3'-indoles and 2,3,4,9-tetrahydro-1H-carbazoles by iridium-catalyzed allylic dearomatization and stereospecific migration.

  2012cited by this paper
• Copper(I)-catalyzed cascade dearomatization of 2-substituted tryptophols with iodonium [corrected] salts.

  2012cited by this paper
• Organocatalyzed enantioselective fluorocyclizations.

  2011cited by this paper
• A Practical and Enantioselective Approach to Tetrahydrocarbazoles by Asymmetric Organocatalysis

  2011cited by this paper
• Enantioselective Michael/Mannich polycyclization cascade of indolyl enones catalyzed by quinine-derived primary amines.

  2011cited by this paper
• Chiral Brønsted acids in enantioselective carbonyl activations--activation modes and applications.

  2011cited by this paper
• Chiral phosphoric acid-catalysed Friedel–Crafts alkylation reaction of indoles with racemic spiro indolin-3-ones

  2011cited by this paper
• Chiral Phosphoric Acids asVersatile Catalysts for Enantioselective Transformations

  2010cited by this paper
• Chiral Brønsted acid catalyzed asymmetric Friedel-Crafts alkylation reaction of indoles with α,β-unsaturated ketones: short access to optically active 2- and 3-substituted indole derivatives.

  2010cited by this paper
• Chiral BINOL-derived phosphoric acids: privileged Brønsted acid organocatalysts for C-C bond formation reactions.

  2010cited by this paper
• Organocatalytic strategies for the asymmetric functionalization of indoles.

  2010cited by this paper
• Enantioselective construction of spiroindolenines by Ir-catalyzed allylic alkylation reactions.

  2010cited by this paper
• Catalytic functionalization of indoles in a new dimension.

  2009cited by this paper
• Enantioselective synthesis of (3-indolyl)glycine derivatives via asymmetric Friedel–Crafts reaction between indoles and glyoxylate imines

  2009cited by this paper
• Chiral Brønsted acid catalyzed Friedel-Crafts alkylation reactions.

  2009cited by this paper
• An Efficient Enantioselective Method for Asymmetric Friedel–Crafts Alkylation of Indoles with α,β‐Unsaturated Aldehydes

  2009cited by this paper
• Binaphthol-derived phosphoric acid as a versatile catalyst for enantioselective carbon-carbon bond forming reactions.

  2008cited by this paper
• Palladium-catalyzed beta-allylation of 2,3-disubstituted indoles.

  2008cited by this paper
• Chiral phosphoric acid catalyzed enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes: cooperative effect of 3 A molecular sieves.

  2008cited by this paper
• Asymmetric Brønsted acid catalysis: enantioselective nucleophilic substitutions and 1,4-additions.

  2008cited by this paper
• Catalytic asymmetric Friedel-Crafts alkylation reactions--copper showed the way.

  2008cited by this paper
• Stronger Brønsted acids.

  2007cited by this paper
• Organocatalytic enantioselective indole alkylations of alpha,beta-unsaturated ketones.

  2007cited by this paper
• Organocatalytic Asymmetric Friedel−Crafts Alkylation of Indoles with Simple α,β-Unsaturated Ketones

  2007cited by this paper
• Organocatalytic asymmetric Friedel-Crafts alkylation of indoles with simple alpha,beta-unsaturated ketones.

  2007cited by this paper
• Highly enantioselective Friedel-Crafts reaction of indoles with imines by a chiral phosphoric acid.

  2007cited by this paper
• Palladium-catalyzed enantioselective C-3 allylation of 3-substituted-1H-indoles using trialkylboranes.

  2006cited by this paper
• Enantioselective Friedel-Crafts type addition of indoles to nitro-olefins using a chiral hydrogen-bonding catalyst--synthesis of optically active tetrahydro-beta-carbolines.

  2005cited by this paper
• Catalytic enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes by using a simple thiourea organocatalyst.

  2005cited by this paper
• Pd-catalyzed C3-selective allylation of indoles with allyl alcohols promoted by triethylborane.

  2005cited by this paper
• Enantioselective organocatalytic construction of pyrroloindolines by a cascade addition-cyclization strategy: synthesis of (-)-flustramine B.

  2004cited by this paper
• Enantioselective Mannich-type reaction catalyzed by a chiral Brønsted acid.

  2004cited by this paper
• Organocatalytic asymmetric aza-Friedel-Crafts alkylation of furan.

  2004cited by this paper
• Enantioselective organocatalytic indole alkylations. Design of a new and highly effective chiral amine for iminium catalysis.

  2002cited by this paper

• Rearrangement of 5-Indolyl-3-pyrrolin-2-ones into Privileged 4-Indolyl-3-pyrrolin-2-ones Leads to Identification of Antiproliferative Compounds Active under Hypoxia.

  2026cites this paper
• Asymmetric Dearomatization of 3H-Indoles via Copper-Catalyzed Enantioselective [4 + 1] Spiroannulation with Vinyl Ethynylethylene Carbonates.

  2025cites this paper
• Enantioselective Organocatalyzed Cascade Dearomatizing Spirocycloaddition Reactions of Indole-Ynones.

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

  2024cites this paper
• Diversity-Oriented Synthesis of Indole-Fused Polycyclic Scaffolds via Rhodium-Catalyzed NH-Indole-Directed C-H Coupling of 2-Phenyl-1H-indoles with Propargylic Alcohol Derivatives.

  2024cites this paper
• Expedient Access to Enantioenriched 1-Azaspiro Cyclobutanones Enabled by Modified Heyns Rearrangement.

  2023cites this paper
• Synthesis of spiroindolenine-cyclopentenedione skeletons and their chemical behaviours: the first example of a lactone-type spiroindolenine structure.

  2022cites this paper
• Synthesis of Spiro[indole-3,3'-pyrrolidine]-2'-(thi)ones.

  2022cites this paper
• Synthesis of Biphenanthrol-Based Confined Chiral Phosphoric Acid

  2022cites this paper
• HFIP-mediated three-component imidization of electron-rich arenes with in situ formed spiroindolenines for facile construction of 2-arylspiroindolenines

  2022cites this paper
• Maleic Acid/Thiourea‐Catalyzed Dearomative ipso ‐Friedel–Crafts Reaction of Indoles to Produce Functionalized Spiroindolenines

  2021cites this paper
• Recent advances in the asymmetric phosphoric acid-catalyzed synthesis of axially chiral compounds

  2021cites this paper
• Total synthesis of (+)-spiroindimicin A and congeners unveils their antiparasitic activity

  2021cites this paper
• Palladium-catalyzed asymmetric [3 + 2] cycloaddition of vinyl aziridines and α,β-unsaturated imines generated in situ from aryl sulfonyl indoles

  2021cites this paper
• Total Synthesis of (+)-Spiroindimicin A via Asymmetric Palladium-Catalyzed Spirocyclization

  2021cites this paper
• Enantioselective Arylation of Tetrasubstituted Enamines: Access to Enantioenriched Indolenine and 1H-Indole Derivatives

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

  2021cites this paper
• Progresses in organocatalytic asymmetric dearomatization reactions of indole derivatives

  2020cites this paper
• Organocatalytic Enantioselective Synthesis of Tetrasubstituted α-Amino Allenoates by Dearomative γ-Addition of β,γ-alkynyl-α-imino esters and 2,3-disubstituted indoles.

  2020cites this paper
• Silver(I) Triflate‐Catalyzed Protocol for the Post‐Ugi Synthesis of Spiroindolines

  2020cites this paper
• Enantioselective Synthesis of Spiroindolines via Cascade Isomerization/Spirocyclization/Dearomatization Reaction.

  2020cites this paper
• Exploring the Chemistry of Spiroindolenines by Mechanistically-Driven Reaction Development: Asymmetric Pictet-Spengler-type Reactions and Beyond.

  2020cites this paper
• Enantioselective Dearomative Cyclization of Homotryptamines with Allenamides into Indolo[2,3‐ b ]quinolines

  2020cites this paper
• Asymmetric N-aminoalkylation of 3-substituted indoles by N-protected N,O-acetals: an access to chiral propargyl aminals.

  2020cites this paper
• Selective Synthesis of Pyrano[3,2-b]indoles or Cyclopenta[b]indoles Tethered with Medium-Sized Rings via Cascade C-C σ-Bond Cleavage and C-H Functionalization.

  2020cites this paper
• Simple primary β-amino alcohols as organocatalysts for the asymmetric Michael addition of β-keto esters to nitroalkenes

  2020cites this paper
• 2-Azanorbornane-Based Amino Alcohol Organocatalysts for Asymmetric Michael Reaction of β-Keto Esters with Nitroolefins

  2019cites this paper
• Highly Diastereo- and Enantioselective Synthesis of Quinuclidine Derivatives by an Iridium-Catalyzed Intramolecular Allylic Dearomatization Reaction

  2019cites this paper
• Catalytic Enantioselective Construction of Spiro Quaternary Carbon Stereocenters

  2019cites this paper
• Chiral phosphoric acid-catalyzed asymmetric dearomatization reactions.

  2019cites this paper
• Synthesis of Functionalized Spirocyclic Indolines by Visible Light‐Induced One‐Pot Sequential Difluoromethylative Dearomatization, Hydroxylation, and Substitution Reactions

  2019cites this paper
• Metal-Free Dearomatization: Direct Access to Spiroindol(en)ines in Batch and Continuous-Flow.

  2019cites this paper
• Redox-Neutral Cascade Dearomatization of Indoles via Hydride Transfer: Divergent Synthesis of Tetrahydroquinoline-Fused Spiroindolenines.

  2019cites this paper
• Specific Synthesis of 3H-Indole Derivatives via Rh(III)-Catalyzed Cascade Annulation between N-phenylbenzimidamides and Pyridotriazoles.

  2019cites this paper
• Controllable Syntheses of Spiroindolenines and Benzazepinoindoles via Hexafluoroisopropanol-Mediated Redox-Neutral Cascade Process.

  2019cites this paper
• Palladium-catalyzed intermolecular allenylation reactions of 2,3-disubstituted indoles and allenyl carbonate.

  2019cites this paper
• Organocatalytic Enantioselective Synthesis of Tetrasubstituted α‐Amino Allenoates by Dearomative γ‐Addition of 2,3‐Disubstituted Indoles to β,γ‐Alkynyl‐α‐imino Esters

  2019cites this paper
• Highly diastereoselective oxa-[3+3] cyclization with C,N-cyclic azomethine imines via the copper-catalyzed aerobic oxygenated C[double bond, length as m-dash]C bond of indoles.

  2018cites this paper
• Manipulation of Spiroindolenine Intermediates for Enantioselective Synthesis of 3-(Indol-3-yl)-Pyrrolidines.

  2018cites this paper
• Chemoselective N-H or C-2 Arylation of Indole-2-carboxamides: Controllable Synthesis of Indolo[1,2- a]quinoxalin-6-ones and 2,3'-Spirobi[indolin]-2'-ones.

  2018cites this paper
• Enantioselectivity in CPA-catalyzed Friedel-Crafts reaction of indole and N-tosylimines: a challenge for guiding models.

  2018cites this paper
• Visible-Light-Promoted Cascade Alkene Trifluoromethylation and Dearomatization of Indole Derivatives via Intermolecular Charge Transfer.

  2018cites this paper
• Dearomatizing Spiroannulation Reagents: Direct Access to Spirocycles from Indoles and Dihalides.

  2018cites this paper
• Recent advances in asymmetric reactions catalyzed by chiral phosphoric acids

  2018cites this paper
• Visible-Light-Mediated Dearomatization/Cyanation Cascade Reaction of Indoles: Access to Highly Functionalized Spiro-γ-lactam Indolines with Two Contiguous Sterically Congested Quaternary Carbon Stereocenters

  2018cites this paper
• Catalytic Asymmetric Dearomatization of Indolyl Dihydropyridines through an Enamine Isomerization/Spirocyclization/Transfer Hydrogenation Sequence.

  2018cites this paper
• Palladium(0)-Catalyzed Intermolecular Asymmetric Allylic Dearomatization of Polycyclic Indoles.

  2018cites this paper
• Synthesis of isatin-conjugated 3H-indole-N-oxides and their serendipitous conversion to spiroindolenines

  2018cites this paper
• Reaction of Electron-Deficient 3-Acetyl-1-arylpent-2-ene-1,4-diones as a Building Block of Heterocycles

  2017cites this paper
• Synthesis of C3-Methyl-Substituted Pyrroloindolines and Furoindolines via Cascade Dearomatization of Indole Derivatives with Methyl Iodide.

  2017cites this paper
• Radical Trifluoromethylative Dearomatization of Indoles and Furans with CO2

  2017cites this paper