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Construction of Quaternary Stereogenic Carbon Centers through Copper‐Catalyzed Enantioselective Allylic Alkylation of Azoles

https://doi.org/10.1002/anie.201600619

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What this work says

Outgoing claims: the papers this work cites, builds on, or argues with.

inferredcites →https://doi.org/10.1002/ange.201005124openalex-snapshot

Quaternary Carbon Stereogenic Centers through Copper‐Catalyzed Enantioselective Allylic Substitutions with Readily Accessible Aryl‐ or Heteroaryllithium Reagents and Aluminum Chlorides

inferredcites →https://doi.org/10.1002/ange.201103581openalex-snapshot

Copper‐Catalyzed Asymmetric Allylic Substitution of Allyl Phosphates with Aryl‐ and Alkenylboronates

inferredcites →https://doi.org/10.1002/ange.201200809openalex-snapshot

Regio‐ and Stereocontrolled Introduction of Secondary Alkyl Groups to Electron‐Deficient Arenes through Copper‐Catalyzed Allylic Alkylation

inferredcites →https://doi.org/10.1002/ange.201202856openalex-snapshot

Copper‐Catalyzed Enantioselective Allylic Substitution with Readily Accessible Carbonyl‐ and Acetal‐Containing Vinylboron Reagents

inferredcites →https://doi.org/10.1002/ange.201300785openalex-snapshot

Copper‐Catalyzed γ‐Selective and Stereospecific Direct Allylic Alkylation of Terminal Alkynes: Synthesis of Skipped Enynes

inferredcites →https://doi.org/10.1002/ange.201306824openalex-snapshot

Enantioselective Palladium(II) Phosphate Catalyzed Three‐Component Reactions of Pyrrole, Diazoesters, and Imines

inferredcites →https://doi.org/10.1002/ange.201309207openalex-snapshot

Chiral Cp‐Rhodium(III)‐Catalyzed Asymmetric Hydroarylations of 1,1‐Disubstituted Alkenes

inferredcites →https://doi.org/10.1002/ange.201405252openalex-snapshot

Enantioselective Formation of All‐Carbon Quaternary Stereocenters from Indoles and Tertiary Alcohols Bearing A Directing Group

inferredcites →https://doi.org/10.1002/anie.201005124openalex-snapshot

Quaternary Carbon Stereogenic Centers through Copper‐Catalyzed Enantioselective Allylic Substitutions with Readily Accessible Aryl‐ or Heteroaryllithium Reagents and Aluminum Chlorides

inferredcites →https://doi.org/10.1002/anie.201103581openalex-snapshot

Copper‐Catalyzed Asymmetric Allylic Substitution of Allyl Phosphates with Aryl‐ and Alkenylboronates

inferredcites →https://doi.org/10.1002/anie.201200809openalex-snapshot

Regio‐ and Stereocontrolled Introduction of Secondary Alkyl Groups to Electron‐Deficient Arenes through Copper‐Catalyzed Allylic Alkylation

inferredcites →https://doi.org/10.1002/anie.201202856openalex-snapshot

Copper‐Catalyzed Enantioselective Allylic Substitution with Readily Accessible Carbonyl‐ and Acetal‐Containing Vinylboron Reagents

inferredcites →https://doi.org/10.1002/anie.201300785openalex-snapshot

Copper‐Catalyzed γ‐Selective and Stereospecific Direct Allylic Alkylation of Terminal Alkynes: Synthesis of Skipped Enynes

inferredcites →https://doi.org/10.1002/anie.201306824openalex-snapshot

Enantioselective Palladium(II) Phosphate Catalyzed Three‐Component Reactions of Pyrrole, Diazoesters, and Imines

inferredcites →https://doi.org/10.1002/anie.201309207openalex-snapshot

Chiral Cp‐Rhodium(III)‐Catalyzed Asymmetric Hydroarylations of 1,1‐Disubstituted Alkenes

inferredcites →https://doi.org/10.1002/anie.201405252openalex-snapshot

Enantioselective Formation of All‐Carbon Quaternary Stereocenters from Indoles and Tertiary Alcohols Bearing A Directing Group

inferredcites →https://doi.org/10.1002/chem.201302576openalex-snapshot

Asymmetric C(sp2)H Activation

inferredcites →https://doi.org/10.1002/ejoc.200800025openalex-snapshot

Copper‐Catalyzed Asymmetric Allylic Alkylation

inferredcites →https://doi.org/10.1002/ejoc.200901129openalex-snapshot

Enantioselective Fujiwara–Moritani Indole and Pyrrole Annulations Catalyzed by Chiral Palladium(II)–NicOx Complexes

inferredcites →https://doi.org/10.1021/acs.accounts.5b00092openalex-snapshot

Chiral Cyclopentadienyls: Enabling Ligands for Asymmetric Rh(III)-Catalyzed C–H Functionalizations

inferredcites →https://doi.org/10.1021/cr0683515openalex-snapshot

Enantioselective Copper-Catalyzed Conjugate Addition and Allylic Substitution Reactions

inferredcites →https://doi.org/10.1021/cr068424kopenalex-snapshot

Catalytic Asymmetric Conjugate Addition and Allylic Alkylation with Grignard Reagents

inferredcites →https://doi.org/10.1021/ja00133a011openalex-snapshot

Stereospecific Rearrangement of Optically Active Tertiary Allylic Epoxides To Give Optically Active Quaternary Aldehydes: Synthesis of .alpha.-Alkyl Amino Aldehydes and Acids

inferredcites →https://doi.org/10.1021/ja054109oopenalex-snapshot

Highly Enantioselective Synthesis of Tetrahydro-β-Carbolines and Tetrahydro-γ-Carbolines Via Pd-Catalyzed Intramolecular Allylic Alkylation

inferredcites →https://doi.org/10.1021/ja106829kopenalex-snapshot

Synthesis of Quaternary Carbon Stereogenic Centers through Enantioselective Cu-Catalyzed Allylic Substitutions with Vinylaluminum Reagents

inferredcites →https://doi.org/10.1021/ja211269wopenalex-snapshot

Site- and Enantioselective Formation of Allene-Bearing Tertiary or Quaternary Carbon Stereogenic Centers through NHC–Cu-Catalyzed Allylic Substitution

inferredcites →https://doi.org/10.1021/ja308742xopenalex-snapshot

Ir(I)-Catalyzed C–H Bond Alkylation of C2-Position of Indole with Alkenes: Selective Synthesis of Linear or Branched 2-Alkylindoles

inferredcites →https://doi.org/10.1021/ja312360copenalex-snapshot

Iridium-Catalyzed Intermolecular Asymmetric Hydroheteroarylation of Bicycloalkenes

inferredcites →https://doi.org/10.1021/ja400650mopenalex-snapshot

Highly Enantioselective Construction of Trifluoromethylated All-Carbon Quaternary Stereocenters via Nickel-Catalyzed Friedel–Crafts Alkylation Reaction

inferredcites →https://doi.org/10.1021/ja410424gopenalex-snapshot

All-Carbon Quaternary Stereogenic Centers in Acyclic Systems through the Creation of Several C–C Bonds per Chemical Step

inferredcites →https://doi.org/10.1021/ja504995fopenalex-snapshot

Enantioselective C–H Bond Addition of Pyridines to Alkenes Catalyzed by Chiral Half-Sandwich Rare-Earth Complexes

inferredcites →https://doi.org/10.1021/ja5084333openalex-snapshot

Copper-Catalyzed Enantioselective Allylic Alkylation of Terminal Alkyne Pronucleophiles

inferredcites →https://doi.org/10.1021/ja510980dopenalex-snapshot

Organocatalytic Asymmetric Synthesis of 1,1-Diarylethanes by Transfer Hydrogenation

inferredcites →https://doi.org/10.1021/jacs.5b05805openalex-snapshot

N-Heterocyclic Carbene–Copper-Catalyzed Group-, Site-, and Enantioselective Allylic Substitution with a Readily Accessible Propargyl(pinacolato)boron Reagent: Utility in Stereoselective Synthesis and Mechanistic Attributes

inferredcites →https://doi.org/10.1021/jacs.5b11335openalex-snapshot

Enantioselective Dehydrogenative Heck Arylations of Trisubstituted Alkenes with Indoles to Construct Quaternary Stereocenters

inferredcites →https://doi.org/10.1021/ol300274uopenalex-snapshot

High-Pressure Accelerated Asymmetric Organocatalytic Friedel–Crafts Alkylation of Indoles with Enones: Application to Quaternary Stereogenic Centers Construction

inferredcites →https://doi.org/10.1021/ol503119zopenalex-snapshot

Cobalt-Catalyzed Enantioselective Directed C–H Alkylation of Indole with Styrenes

inferredcites →https://doi.org/10.1038/nature14007openalex-snapshot

Catalytic enantioselective synthesis of quaternary carbon stereocentres

inferredcites →https://doi.org/10.1038/nchem.1406openalex-snapshot

Highly enantioselective trapping of zwitterionic intermediates by imines

inferredcites →https://doi.org/10.1039/b816707aopenalex-snapshot

Transition metal-catalyzed C–H activation reactions: diastereoselectivity and enantioselectivity

inferredcites →https://doi.org/10.1039/c0cc05222aopenalex-snapshot

Enantioselective synthesis of all-carbon quaternary stereogenic centers in acyclic systems

inferredcites →https://doi.org/10.1039/c3ra46996dopenalex-snapshot

Recent development of direct asymmetric functionalization of inert C–H bonds

inferredcites →https://doi.org/10.1039/c3sc53542hopenalex-snapshot

Stereoselective construction of all-carbon quaternary center by means of chiral phosphoric acid: highly enantioselective Friedel–Crafts reaction of indoles with β,β-disubstituted nitroalkenes

What points at this work

Incoming claims: where this work appears in other papers’ reference lists and arguments.

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Nucleophilic Aliphatic Substitution

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Carbenes and Nitrenes

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Aromatic Substitution

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Nucleophilic Aliphatic Substitution

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ASYMMETRIC C–H FUNCTIONALIZATION OF C(sp2)–H BOND

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Introduction to High‐Throughput Experimentation (HTE) for the Synthetic Chemist

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Construction of Chiral Tri‐ and Tetra‐Arylmethanes Bearing Quaternary Carbon Centers: Copper‐Catalyzed Enantioselective Propargylation of Indoles with Propargylic Esters

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Copper‐Catalyzed Enantioselective Allyl–Allyl Coupling between Allylic Boronates and Phosphates with a Phenol/N‐Heterocyclic Carbene Chiral Ligand

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Novartis Early Career Award: T. J. Maimone und M. K. Brown / Nagoya‐Goldmedaille: S. L. Buchwald / Nagoya‐Silbermedaille: M. Sawamura

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A Bulky Chiral N‐Heterocyclic Carbene Nickel Catalyst Enables Enantioselective C−H Functionalizations of Indoles and Pyrroles

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Chiral N‐Heterocyclic Carbene Ligands Enable Asymmetric C−H Bond Functionalization

inferred← citeshttps://doi.org/10.1002/ange.202009323openalex-snapshot

Light‐Promoted Copper‐Catalyzed Enantioselective Alkylation of Azoles

inferred← citeshttps://doi.org/10.1002/ange.202009527openalex-snapshot

Copper‐Catalyzed Enantioconvergent Cross‐Coupling of Racemic Alkyl Bromides with Azole C(sp2)−H Bonds

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Catalytic Asymmetric Allylic Substitution with Copper(I) Homoenolates Generated from Cyclopropanols

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Construction of Chiral Tri‐ and Tetra‐Arylmethanes Bearing Quaternary Carbon Centers: Copper‐Catalyzed Enantioselective Propargylation of Indoles with Propargylic Esters

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Copper‐Catalyzed Enantioselective Allyl–Allyl Coupling between Allylic Boronates and Phosphates with a Phenol/N‐Heterocyclic Carbene Chiral Ligand

inferred← citeshttps://doi.org/10.1002/anie.201611502openalex-snapshot

Novartis Early Career Award: T. J. Maimone and M. K. Brown / Nagoya Gold Medal: S. L. Buchwald / Nagoya Silver Medal: M. Sawamura

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Enantioselective C−H Activation with Earth‐Abundant 3d Transition Metals

inferred← citeshttps://doi.org/10.1002/anie.201904774openalex-snapshot

A Bulky Chiral N‐Heterocyclic Carbene Nickel Catalyst Enables Enantioselective C−H Functionalizations of Indoles and Pyrroles

inferred← citeshttps://doi.org/10.1002/anie.201911898openalex-snapshot

Chiral N‐Heterocyclic Carbene Ligands Enable Asymmetric C−H Bond Functionalization

inferred← citeshttps://doi.org/10.1002/anie.202009323openalex-snapshot

Light‐Promoted Copper‐Catalyzed Enantioselective Alkylation of Azoles

inferred← citeshttps://doi.org/10.1002/anie.202009527openalex-snapshot

Copper‐Catalyzed Enantioconvergent Cross‐Coupling of Racemic Alkyl Bromides with Azole C(sp2)−H Bonds

inferred← citeshttps://doi.org/10.1002/anie.202110709openalex-snapshot

Catalytic Asymmetric Allylic Substitution with Copper(I) Homoenolates Generated from Cyclopropanols

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Synergistic Pd/Cu Catalysis in Organic Synthesis

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ChemInform Abstract: Construction of Quaternary Stereogenic Carbon Centers Through Copper‐Catalyzed Enantioselective Allylic Alkylation of Azoles.

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inferred← citeshttps://doi.org/10.1021/acs.chemrev.6c00255openalex-snapshot

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Acyclic Quaternary Carbon Stereocenters via Enantioselective Transition Metal Catalysis

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3d Transition Metals for C–H Activation

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