Well-defined binuclear chiral spiro copper catalysts for enantioselective N-H insertion.

No abstract is available for this paper.

• Publication year

  2012

• Venue

  Journal of the American Chemical Society

• Publication date

  2012-01-11

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/ja2084493PMID 22066865
• 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.

• Diastereoselectively switchable enantioselective trapping of carbamate ammonium ylides with imines.

  2011cited by this paper
• Highly enantioselective cyclopropenation reaction of 1-alkynes with α-alkyl-α-diazoesters catalyzed by dirhodium(II) carboxylates.

  2011cited by this paper
• Palladium-catalyzed carbonylation/acyl migratory insertion sequence.

  2010cited by this paper
• Enantioselective copper-catalyzed intramolecular O-H insertion: an efficient approach to chiral 2-carboxy cyclic ethers.

  2010cited by this paper
• Catalytic asymmetric Roskamp reaction of alpha-alkyl-alpha-diazoesters with aromatic aldehydes: highly enantioselective synthesis of alpha-alkyl-beta-keto esters.

  2010cited by this paper
• Chiral Induction by cinchona alkaloids in the rhodium(II) catalyzed O-H insertion reaction.

  2010cited by this paper
• Highly enantioselective insertion of carbenoids into N-H bonds catalyzed by copper(I) complexes of binol derivatives.

  2010cited by this paper
• Asymmetric Intermolecular N—H Insertion Reaction of Phenyldiazoacetates with Anilines Catalyzed by Achiral Dirhodium(II) Carboxylates and Cinchona Alkaloids.

  2010cited by this paper
• Enantioselective iron-catalysed O–H bond insertions

  2010cited by this paper
• Metallopeptides for asymmetric dirhodium catalysis.

  2010cited by this paper
• Use of Diphenyliodonium Bromide in the Synthesis of Some N-Phenyl α-Amino Acids

  2010cited by this paper
• Cooperative catalysis in multicomponent reactions: highly enantioselective synthesis of gamma-hydroxyketones with a quaternary carbon stereocenter.

  2010cited by this paper
• Iridium(III)-catalyzed enantioselective Si-H bond insertion and formation of an enantioenriched silicon center.

  2010cited by this paper
• One-pot three-component tandem reaction of diazo compounds with anilines and unsaturated ketoesters: a novel synthesis of 2,3-dihydropyrrole derivatives.

  2009cited by this paper
• Why is copper(I) complex more competent than dirhodium(II) complex in catalytic asymmetric O-H insertion reactions? A computational study of the metal carbenoid O-H insertion into water.

  2009cited by this paper
• Iridium/monodentate phosphoramidite catalyzed asymmetric hydrogenation of N-aryl imines.

  2009cited by this paper
• Copper-catalyzed enantioselective carbenoid insertion into S-H bonds.

  2009cited by this paper
• Ruthenium-catalyzed one-pot carbenoid N-H insertion reactions and diastereoselective synthesis of prolines.

  2008cited by this paper
• Copper-catalyzed highly enantioselective carbenoid insertion into Si-H bonds.

  2008cited by this paper
• Catalytic asymmetric reaction with water: enantioselective synthesis of alpha-hydroxyesters by a copper-carbenoid O-H insertion reaction.

  2008cited by this paper
• The herbicide flamprop-M-methyl has a new antimicrotubule mechanism of action.

  2008cited by this paper
• Convenient synthetic route to an enantiomerically pure FMOC alpha-amino acid.

  2008cited by this paper
• Recent studies on the reactions of α-diazocarbonyl compounds

  2008cited by this paper
• Palladium-catalyzed cross-coupling of alpha-diazocarbonyl compounds with arylboronic acids.

  2008cited by this paper
• Efficient trapping of oxonium ylides with imines: a highly diastereoselective three-component reaction for the synthesis of beta-amino-alpha-hydroxyesters with quaternary stereocenters.

  2007cited by this paper
• Catalytic asymmetric synthesis of alpha-amino acids.

  2007cited by this paper
• Catalytic Asymmetric Synthesis of α-Amino Acids

  2007cited by this paper
• Copper-catalyzed asymmetric N-H insertion reactions: couplings of diazo compounds with carbamates to generate alpha-amino acids.

  2007cited by this paper
• Efficient Trapping of Oxonium Ylides with Imines: A Highly Diastereoselective Three‐Component Reaction for the Synthesis of β‐Amino‐α‐hydroxyesters with Quaternary Stereocenters

  2007cited by this paper
• Copper-Catalyzed Asymmetric N−H Insertion Reactions: Couplings of Diazo Compounds with Carbamates to Generate α-Amino Acids

  2007cited by this paper
• Highly enantioselective insertion of carbenoids into N-H bonds catalyzed by copper complexes of chiral spiro bisoxazolines.

  2007cited by this paper
• Highly enantioselective insertion of carbenoids into O-H bonds of phenols: an efficient approach to chiral alpha-aryloxycarboxylic esters.

  2007cited by this paper
• Enantioselective insertion of metal carbenes into N-H bonds: a potentially versatile route to chiral amine derivatives.

  2007cited by this paper
• Catalytic enantioselective O-H insertion reactions.

  2006cited by this paper
• Three-component reaction of aryl diazoacetates, alcohols, and aldehydes (or imines): evidence of alcoholic oxonium ylide intermediates.

  2005cited by this paper
• Rhodium‐Catalyzed, Three‐Component Reaction of Diazo Compounds with Amines and Azodicarboxylates

  2005cited by this paper
• Novel C–C bond formation through addition of ammonium ylides to arylaldehydes: a facile approach to β-aryl-β-hydroxy α-amino acid frameworks

  2004cited by this paper
• Novel C-C bond formation through addition of ammonium ylides to arylaldehydes: a facile approach to beta-aryl-beta-hydroxy alpha-amino acid frameworks.

  2004cited by this paper
• Metal carbene N–H insertion of chiral α,α′-dialkyl α-diazoketones. A novel and concise method for the stereocontrolled synthesis of fully substituted azetidines ☆

  2004cited by this paper
• Cu(I)-carbenoid- and Ag(I)-Lewis acid-catalyzed asymmetric intermolecular insertion of alpha-diazo compounds into N-H bonds.

  2004cited by this paper
• A novel three-component reaction catalyzed by dirhodium(II) acetate: decomposition of phenyldiazoacetate with arylamine and imine for highly diastereoselective synthesis of 1,2-diamines.

  2003cited by this paper
• Mechanism of C[bond]H bond activation/C[bond]C bond formation reaction between diazo compound and alkane catalyzed by dirhodium tetracarboxylate.

  2002cited by this paper
• Rhodium chemzymes: Michaelis-Menten kinetics in dirhodium(II) carboxylate-catalyzed carbenoid reactions.

  2002cited by this paper
• Asymmetric synthesis of substituted prolines from delta-amino beta-ketoesters. Methyl (2S,5R)-(+)-5-phenylpyrrolidine-2-carboxylate.

  2002cited by this paper
• Mechanism of C-H Bond Activation/C-C Bond Formation Reaction between Diazo Compound and Alkane catalyzed by Dirhodium Tetracarboxylate

  2002cited by this paper
• Preparation of chiral α-diazophosphonic acid derivatives

  2001cited by this paper
• Speciation and Mechanistic Studies of Chiral Copper(I) Schiff Base Precursors Mediating Asymmetric Carbenoid Insertion Reactions of Diazoacetates into the Si-H Bond of Silanes

  2000cited by this paper
• Cuprophilicity: Spectroscopic and Structural Evidence for Cu-Cu Bonding Interactions in Luminescent Dinuclear Copper(I) Complexes with Bridging Diphosphane Ligands We are grateful for financial support from The University of Hong Kong, the Hong Kong University Foundation, and the Research Grants Cou

  2000cited by this paper
• Mechanism of metal-carbenoid insertion into the SiH bond

  1997cited by this paper
• A Convenient Method for the Preparation of (Z)-alpha,beta-Unsaturated Carbonyl Compounds.

  1996cited by this paper
• Asymmetric catalysis of intramolecular N–H insertion reactions of α-diazocarbonyls

  1996cited by this paper
• Predicting the Diastereoselectivity of Rh-Mediated Intramolecular C−H Insertion

  1996cited by this paper
• Model Studies of the Stereoelectronic Effect in Rh(II) Mediated Carbenoid C-H Insertion Reactions

  1994cited by this paper
• Electronic and steric control in carbon-hydrogen insertion reactions of diazoacetoacetates catalyzed by dirhodium(II) carboxylates and carboxamides

  1993cited by this paper
• Rhodium-mediated cyclopentane construction can compete with .beta.-hydride elimination: synthesis of (.+-.)-tochuinyl acetate

  1992cited by this paper
• A survey of Hammett substituent constants and resonance and field parameters

  1991cited by this paper
• N-phenylation of amino acid derivatives

  1989cited by this paper
• Une nouvelle synthese asymetrique de l'alanine par insertion d'un carbene sur une liaison N-H.

  1971cited by this paper
• The Copper-catalyzed Decomposition of Diazoketones1

  1952cited by this paper

• Recent progress in transition-metal-catalysed intermolecular saturated C(sp3)-N(sp3) bond formation reactions.

  2026cites this paper
• Molybdenum‐Catalyzed Asymmetric Amination of α‐Hydroxy Esters: Synthesis of α‐Amino Acids

  2025cites this paper
• Dirhodium-Palladium Dual-Catalyzed [1 + 1 + 3] Annulation to Heterocycles Using Primary Amines or H2O as the Heteroatom Sources.

  2025cites this paper
• Enantioselective Copper-Catalyzed N-H Insertion Reaction of Pyrazoles and α-Diazo Phosphates.

  2025cites this paper
• Carbene transfer reactions enabled by heterogeneous metal catalysis.

  2025cites this paper
• Effective Coordination Promoted Carbene N─H Bond Insertion on Heterogeneous Cu Catalyst.

  2025cites this paper
• Cu-Catalyzed Asymmetric Carbene Insertion into N–H, O–H, and S–H Bonds: Challenging the Existing Mechanistic Dogma

  2025cites this paper
• Cobaloxime catalyzed carbene insertion into N–H bonds: a streamlined route to α-amino esters with mechanistic insights

  2025cites this paper
• Enantioselective N-H Insertion of Sulfonamides: Access to Chiral α-Aminoesters.

  2025cites this paper
• Multifunctional chiral silanol ligands for enantioselective catalysis

  2025cites this paper
• Enantioselective synthesis of chiral amides by carbene insertion into amide N–H bond

  2024cites this paper
• Rh-Catalyzed Chemodivergent [3+3] Annulations of Diazoenals and α-Aminoketones: Direct Synthesis of Functionalized 1,2-Dihydropyridines and Fused 1,4-Oxazines.

  2024cites this paper
• Highly effective one pot reaction from α-hydrazonoesters to give anilinoesters via α-diazoesters

  2024cites this paper
• Rhodium-catalyzed atropodivergent hydroamination of alkynes by leveraging two potential enantiodetermining steps

  2024cites this paper
• Mechanism and stereoselectivity in metal and enzyme catalyzed carbene insertion into X-H and C(sp2)-H bonds.

  2024cites this paper
• Enantioselective N-H Bond Insertion Reaction of Anilines Enabled by Ruthenium and Chiral Phosphoric Acid Cooperative Catalysis.

  2024cites this paper
• Rhodium(II)-Catalyzed N-H Insertions of Carbenes under Mechanochemical Conditions.

  2024cites this paper
• Cu-Catalyzed Cross-Electrophilic Coupling of α-Diazoesters with O-Benzoyl Hydroxylamines for the Synthesis of Unnatural N-Alkyl α-Amino Acid Derivatives.

  2023cites this paper
• Well-defined chiral dinuclear copper complexes in enantioselective propargylic substitution: For a long-standing supposition on binuclear mechanism

  2023cites this paper
• Is Enol Always the Culprit? The Curious Case of High Enantioselectivity in a Chiral Rh(II) Complex Catalyzed Carbene Insertion Reaction.

  2023cites this paper
• New Insights into the Cooperativity and Dynamics of Dimeric Enzymes.

  2023cites this paper
• Diruthenium Tetracarboxylate-Catalyzed Enantioselective Cyclopropanation with Aryldiazoacetates

  2023cites this paper
• Nitrile formation via dichlorocarbene insertion into the Si-N bond of Ln(III) bis(trimethylsilyl)amide complexes.

  2022cites this paper
• Palladium-Catalyzed Three-Component Selective Aminoallylation of Diazo Compounds.

  2022cites this paper
• Does an Enol Pathway Preclude High Stereoselectivity in Iron-Catalyzed Indole C-H Functionalization via Carbene Insertion?

  2022cites this paper
• DFT rationalization of metal-catalyst-controlled coupling of carbazole with diazo-naphthalen-2(1H)-one

  2022cites this paper
• Advances of Chiral Spiro Skeleton-Based Bisnitrogen Ligands in Transition-Metal Catalysis

  2022cites this paper
• Exploiting the Chiral Ligands of Bis(imidazolinyl)- and Bis(oxazolinyl)thiophenes—Synthesis and Application in Cu-Catalyzed Friedel–Crafts Asymmetric Alkylation

  2021cites this paper
• Catalytic Enantioselective Carbene Insertions into Heteroatom–Hydrogen Bonds

  2021cites this paper
• Reactions of Ylides Generated from M C Bonds

  2021cites this paper
• Rationalization of the mechanism and chemoselectivity of versatile Au-catalyzed reactions of diazoesters with allyl-functionalized sulfides, selenides, amines, or ethers by DFT

  2021cites this paper
• Transition metal-catalyzed asymmetric carbene insertion for synthesis of chiral amines

  2021cites this paper
• Additions of N, O, and S heteroatoms to metal-supported carbenes: Mechanism and synthetic applications in modern organic chemistry

  2021cites this paper
• Blue light-promoted cyclopropenizations of N-tosylhydrazones in water

  2021cites this paper
• Enantioselective Formal Vinylogous N-H Insertion of Secondary Aliphatic Amines Catalyzed by a High-Spin Cobalt(II) Complex.

  2021cites this paper
• Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis

  2021cites this paper
• Rhodium‐Catalyzed O−H Bond Insertion Reaction between H‐Phosphoryl Compounds and 2‐Pyridyl Carbenes Generated from Pyridotriazoles

  2021cites this paper
• Asymmetric Synthesis of N‐Substituted α‐Amino Esters from α‐Ketoesters via Imine Reductase‐Catalyzed Reductive Amination

  2021cites this paper
• Cu/PCy3‐Catalyzed Formal Carbene Insertion into Electron‐Deficient C−H Bonds

  2020cites this paper
• Chiral diene-promoted room temperature conjugate arylation: highly enantioselective synthesis of substituted chiral phenylalanine derivatives and α,α-di(arylmethyl)acetates.

  2020cites this paper
• Turning Waste into Valuable Catalysts: Application of Surface-Modified Sewage Sludge in N–H Insertion Reaction

  2020cites this paper
• Recent Progress towards the Use of Benzophenone Imines as an Ammonia Equivalent

  2020cites this paper
• Copper(I) catalyzed CO2 transformation: A density functional theory investigation

  2020cites this paper
• TfOH-Catalyzed N-H Insertion of α-Substituted-α-Diazoesters with Anilines Provides Access to Unnatural α-Amino Esters.

  2020cites this paper
• Rare-earth metal–organic frameworks as advanced catalytic platforms for organic synthesis

  2020cites this paper
• Copper-catalyzed N–H insertion reactions from sulfoxonium ylides

  2020cites this paper
• Planar Chiral [2.2]Paracyclophane-Based Bisoxazoline Ligands and Their Applications in Cu-Mediated N–H Insertion Reaction

  2019cites this paper
• A Cyclohexyl-Fused Spirobiindane-derived Phosphine-catalyzed Synthesis of Tricyclic γ-Lactams and Kinetic Resolution of γ-Substituted Allenoates.

  2019cites this paper
• Enantioselective carbene insertion into the N–H bond of benzophenone imine† †Electronic supplementary information (ESI) available. CCDC 1915990 and 1935053. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c9sc03354h

  2019cites this paper
• Preparation of Axially Chiral 2,2'-Biimidazole Ligands through Remote Chirality Delivery and Their Application in Asymmetric Carbene Insertion into N-H of Carbazoles.

  2019cites this paper
• Substituent-oriented C-N bond formation via N-H insertion or Wolff rearrangement of 5-aryl-1H-pyrazoles and diazo compounds.

  2019cites this paper
• Highly enantioselective carbene insertion into N–H bonds of aliphatic amines

  2019cites this paper
• Reactions of 5-Aminoisoxazoles with α-Diazocarbonyl Compounds: Wolff Rearrangement vs N-H Insertion.

  2019cites this paper
• Carbene insertion into N-H bonds with size-selectivity induced by a microporous ruthenium-porphyrin metal-organic framework.

  2018cites this paper
• Carbene Transfer and Carbene Insertion Reactions Catalyzed by a Mixed-Ligand Copper(I) Complex

  2018cites this paper
• Intermolecular Acetoxyaminoalkylation of α-Diazo Amides with (Diacetoxyiodo)benzene and Amines.

  2018cites this paper
• Planar Chiral [2.2]Paracyclophane-Based Bisoxazoline Ligands: Design, Synthesis, and Use in Cu-Catalyzed Inter- and Intramolecular Asymmetric O-H Insertion Reactions.

  2018cites this paper
• Blue light-promoted photolysis of aryldiazoacetates

  2018cites this paper
• Silver-catalyzed regioselective hydroamination of alkenyl diazoacetates to synthesize γ-amino acid equivalents.

  2018cites this paper
• Chiral Cyclohexyl-Fused Spirobiindanes: Practical Synthesis, Ligand Development, and Asymmetric Catalysis.

  2018cites this paper
• Beyond a solvent: triple roles of dimethylformamide in organic chemistry

  2018cites this paper
• Gold-catalyzed highly regio- and enantioselective vinylcarbene insertion into O-H bonds of 2-pyridones.

  2017cites this paper
• Synthesis of azasilacyclopentenes and silanols via Huisgen cycloaddition-initiated C–H bond insertion cascades

  2017cites this paper
• 6-Hydroxynorleucine: Syntheses and Applications of a Versatile Building Block

  2017cites this paper
• Tetrakis(acetonitrile)copper(I) Hexafluorophosphate

  2017cites this paper
• Iridium catalyzed acceptor/acceptor carbene insertion into N-H bonds in water.

  2017cites this paper
• Copper-Catalyzed Insertion into Heteroatom-Hydrogen Bonds with Trifluorodiazoalkanes.

  2016cites this paper
• A Green Approach to the Synthesis of α-Amino Phosphonate in Water Medium: Carbene Insertion into the N-H Bond by Cu(I) Catalyst.

  2016cites this paper
• A Cu-catalyzed four-component cascade reaction to construct β-ester-γ-amino ketones.

  2016cites this paper
• Asymmetric O–H insertion reaction of carbenoids catalyzed by chiral bicyclo bisoxazoline copper(I) and (II) complexes

  2016cites this paper
• Copper(I) catalyzed diastereoselective multicomponent synthesis of spiroindolo-pyrrolidines/-imidazolidines/-triazolidines from diazoamides via azomethine ylides.

  2016cites this paper
• Spiro Ligands for Asymmetric Catalysis

  2016cites this paper
• Phosphine ligands stabilized Cu(I) catalysts for carbene insertion into the N–H bond

  2016cites this paper
• Synthesis of Acyclic Nucleoside Analogues through the Insertion of Carbenoids into N−H Bond of Nucleobases

  2016cites this paper
• Chapter Two – Recent Advances in Asymmetric Metal-Catalyzed Carbene Transfer from Diazo Compounds Toward Molecular Complexity

  2016cites this paper
• Asymmetric Intramolecular Desymmetrization of meso-α,α'-Diazido Alcohols with Aryldiazoacetates: Assembly of Chiral C3 Fragments with Three Continuous Stereocenters.

  2016cites this paper
• Synthesis of Aminobenzoic Acid Derivatives via Chemoselective Carbene Insertion into the -NH Bond Catalyzed by Cu(I) Complex.

  2016cites this paper
• Development of a Method for the N-Arylation of Amino Acid Esters with Aryl Triflates

  2016cites this paper
• A series of robust metal-porphyrinic frameworks based on rare earth clusters and their application in N-H carbene insertion.

  2016cites this paper
• Aminofluorination: transition-metal-free N–F bond insertion into diazocarbonyl compounds

  2015cites this paper
• Rhodium(I)-catalyzed asymmetric carbene insertion into B-H bonds: highly enantioselective access to functionalized organoboranes.

  2015cites this paper
• Modular construction of multifunctional ligands for the enantioselective ruthenium-catalyzed carbenoid N–H insertion reaction: an enzyme-like and substrate-sensitive catalyst system

  2015cites this paper
• Architectural diversity of six coordination compounds based on (S)-(+)-mandelic acid and different N-donor auxiliary ligands: syntheses, structures, and luminescent properties

  2015cites this paper
• Hemin‐Catalyzed, Cyclodextrin‐Assisted Insertion of Carbenoids into NH Bonds

  2015cites this paper
• Enantioselective synthesis of α-alkenyl α-amino acids via N–H insertion reactions

  2015cites this paper
• Chemoselective Carbene insertion into the N-H Bond over O-H Bond Using a Well-Defined Single Site (P-P)Cu(I) Catalyst.

  2015cites this paper
• Enantioselective Insertion of Carbenoids into N—H Bonds Catalyzed by Chiral Bicyclobisoxazoline Copper(I) Complexes.

  2015cites this paper
• Development of Ar-BINMOL-Derived Atropisomeric Ligands with Matched Axial and sp(3) Central Chirality for Catalytic Asymmetric Transformations.

  2015cites this paper
• Stereoselective Synthesis of Arylglycine Derivatives via Palladium-Catalyzed α-Arylation of a Chiral Nickel(II) Glycinate.

  2015cites this paper
• Modern Organic Synthesis with α-Diazocarbonyl Compounds.

  2015cites this paper
• Asymmetric N-H insertion of secondary and primary anilines under the catalysis of palladium and chiral guanidine derivatives.

  2014cites this paper
• Highly site-selective direct C-H bond functionalization of phenols with α-aryl-α-diazoacetates and diazooxindoles via gold catalysis.

  2014cites this paper
• Synergistic rhodium(II) carboxylate and brønsted acid catalyzed multicomponent reactions of enalcarbenoids: direct synthesis of α-pyrrolylbenzylamines.

  2014cites this paper
• Recent Developments in the Synthetic Uses of Silyl-protected Enoldiazoacetates for Heterocyclic Syntheses

  2014cites this paper
• Unexpected Stereoselective Synthesis of (Z)‐β‐Alkenyl Substituted β‐Amino Phosphonates through β,γ‐Dihydrogen Shift Reaction Catalyzed by a Copper(I) Complex and Iodine [Cu(MeCN)4]PF6/I2

  2014cites this paper
• Synthesis of Biologically Relevant Compounds by Ruthenium Porphyrin Catalyzed Amination of Benzylic C–H Bonds

  2014cites this paper
• The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2012

  2014cites this paper
• Mechanistic Insight into Asymmetric N–H Insertion Cooperatively Catalyzed by a Dirhodium Compound and a Spiro Chiral Phosphoric Acid

  2014cites this paper
• Regiospecific and highly stereoselective synthesis of β-amino (Z)-enylphosphonates via β-hydrogen migration reaction of dialkyl α-diazophosphonates catalyzed by AgOTf

  2014cites this paper
• Highly enantioselective Friedel–Crafts alkylation of indole with electron deficient trans-β-nitroalkenes using Zn(II)–oxazoline–imidazoline catalysts

  2014cites this paper