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Catalytic Enantioselective C−H Activation by Means of Metal−Carbenoid-Induced C−H Insertion

https://doi.org/10.1021/cr0200217
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C−C Bond Formation via C−H Bond Activation:  Catalytic Arylation and Alkenylation of Alkane Segments
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Rhodium(II)‐Catalyzed CH Insertions with {[(4‐Nitrophenyl)sulfonyl]imino}phenyl‐λ<sup>3</sup>‐iodane
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Enantioselective carbocyclization: a facile route to chiral cyclopentanes
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Enantioselective Synthesis of a 1,2-Disubstituted Mitosene by a Copper-Catalyzed Intramolecular Carbon-Hydrogen Insertion Reaction of a Diazo Ester
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Asymmetric approaches to 1,2-disubstituted mitosenes based on the intramolecular cyclization of diazoesters
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Steric and Electronic Influences on the Diastereoselectivity of the Rh<sub>2</sub>(OAc)<sub>4</sub>-Catalyzed C−H Insertion in Chiral Ester Diazoanilides:  Synthesis of Chiral, Nonracemic 4-Substituted 2-Pyrrolidinones
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Homochiral group transfer in organic synthesis viaα-diazocarbonyl intermediates
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First Example of Intramolecular C-H Insertion Reaction in an Amino Acid Derived α-Diazoketone
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A Novel Synthetic Route to Chiral γ-Lactams from α-Amino Acids via Rh-Catalyzed Intramolecular C−H Insertion
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Chemo- and stereoselective dirhodium(II)-catalyzed C-H insertion reaction of 5,6-dioxygenated 2-diazo-3-oxohexanoates: Synthesis of an optically active highly functionalized cyclopentane
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C−H Insertion Approach to the Synthesis of <i>e</i><i>ndo,</i><i>e</i><i>xo</i>-Furofuranones:  Synthesis of (±)-Asarinin, (±)-Epimagnolin A, and (±)-Fargesin
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An Enantioselective 1,2-Aziridinomitosene Synthesis via a Chemoselective Carbon−Hydrogen Insertion Reaction of a Metal Carbene
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A Concise Synthesis of (+)-α-Allokainic Acid via Site- and Diastereoselective Intramolecular C-H Insertion Process
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Cyclohexenone Annelation by Alkylidene C−H Insertion:  Synthesis of Oxo-<i>T</i>-cadinol
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Cyclohexenone Construction by Intramolecular Alkylidene C−H Insertion:  Synthesis of (+)-Cassiol
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Enantioselective Construction of Cyclic Quaternary Centers:  (−)-Mesembrine
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Predicting the Diastereoselectivity of Rh-Mediated Intramolecular C−H Insertion
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Regiospecific control of Rh(II) carbenoids in the C-H insertion reaction
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Enantioselective ring construction: synthesis of (+)-.alpha.-cuparenone
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[3+4] annulation between rhodium-stabilized vinylcarbenoids and dienes
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Asymmetric Intermolecular Carbenoid C−H Insertions Catalyzed by Rhodium(II) (<i>S</i>)-<i>N-</i>(<i>p</i>-Dodecylphenyl)sulfonylprolinate
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Mechanism of C−H Bond Activation/C−C Bond Formation Reaction between Diazo Compound and Alkane Catalyzed by Dirhodium Tetracarboxylate
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Ligand Effects on the Chemoselectivity of Ortho-Metalated Rhodium(II) Catalyzed α-Diazo Ketone Transformations
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Dirhodium(II) tetrakis(carboxamidates) with chiral ligands. Structure and selectivity in catalytic metal-carbene transformations
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Synthesis and Structures of (2,2-<i>cis</i>)-Dirhodium(II) Tetrakis[methyl 1-acyl-2-oxoimidazolidine-4(<i>S</i>)-carboxylates]. Chiral Catalysts for Highly Stereoselective Metal Carbene Transformations
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New catalysts and methods for highly enantioselective metal carbene reactions
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First attempts at differential diastereoselection in catalytic reactions of N-chirally substituted dirhodium(ii) tetrakis[methyl 2-oxoimidazolidine-4(S)-carboxylates] with diazoacetates
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Reactivity Enhancement for Chiral Dirhodium(II) Tetrakis(Carboxamidates)
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Dirhodium(II) Tetrakis[methyl 2-oxaazetidine-4-carboxylate]:  A Chiral Dirhodium(II) Carboxamidate of Exceptional Reactivity and Selectivity
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Enantiocontrol in catalytic metal carbene reactions
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Dirhodium(II) Tetrakis[3(S)-phthalimido-2-piperidinonate]: A Novel Dirhodium(II) Carboxamidate Catalyst for Asymmetric Cyclopropanation
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Efficient RhII binaphthol phosphate catalysts for enantioselective intramolecular tandem carbonyl ylide formation–cycloaddition of α-diazo-β-keto esters
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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
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Cyclopropanation versus carbon–hydrogen insertion. The influences of substrate and catalyst on selectivity
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Selectivity in Reactions of Allyl Diazoacetates as a Function of Catalyst and Ring Size from γ-Lactones to Macrocyclic Lactones
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Synthesis of pyrrolizidine bases by highly diastereoselective and regioselective catalytic carbon-hydrogen insertion reactions of chiral pyrrolidinediazoacetamides
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A Dirhodium(II)−Carbenoid Route to (−)- and (+)-Geissman−Waiss Lactone:  Synthesis of (1<i>R</i>,7<i>R</i>,8<i>R</i>)-(−)-Turneforcidine
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Rhodium(II)- and Copper(I)-Catalyzed Intramolecular Carbon-Hydrogen Bond Insertions with Metal Carbenoids Derived from Diazo Ketones
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New Catalysts and Conditions for a CH Insertion Reaction Identified by High Throughput Catalyst Screening
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Enantioselective Synthesis of <scp>d</scp><i>-threo-</i>Methylphenidate
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Chiral catalysts for enantioselective carbenoid cyclopropanation reactions
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Stereoselective synthesis of disubstituted 3(2H)-furanones via catalytic intramolecular C-H insertion reactions of α-diazo-β-keto esters including asymmetric induction
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Asymmetric synthesis in carbon–carbon bond forming reactions of α-diazoketones catalysed by homochiral rhodium( <scp>II</scp> ) carboxylates
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Asymmetric synthesis of substituted chromanones via C–H insertion reactions of α-diazoketones catalysed by homochiral rhodium( <scp>II</scp> ) carboxylates
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A Facile Synthesis of Homochiral Rh(II) Carboxylates
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Enantioselective synthesis of vinylcyclopropanes by rhodium(II) catalyzed decomposition of vinyldiazomethanes in the presence of alkenes
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Asymmetric Cyclopropanations by Rhodium(II) <i>N</i>-(Arylsulfonyl)prolinate Catalyzed Decomposition of Vinyldiazomethanes in the Presence of Alkenes. Practical Enantioselective Synthesis of the Four Stereoisomers of 2-Phenylcyclopropan-1-amino Acid
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Catalytic Asymmetric C−H Activation of Alkanes and Tetrahydrofuran
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Effect of diazoalkane structure on the stereoselectivity of rhodium(II) (S)-N-(arylsulfonyl)prolinate catalyzed cyclopropanations
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Chiral catalysts for enantioselective intermolecular cyclopropanation reactions with methyl phenyldiazoacetate. Origin of the solvent effect in reactions catalyzed by homochiral dirhodium(II) prolinates
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Novel dirhodium tetraprolinate catalysts containing bridging prolinate ligands for asymmetric carbenoid reactions
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Synthesis and evaluation of a novel dirhodium tetraprolinate catalyst containing bridging prolinate ligands
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Enantioselecitve intramolecular CH insertion of α-diazo [β-keto esters catalyzed by homochiral rhodium(II) carboxylates
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Enantio- and Diastereoselective Synthesis of <i>cis</i>-2-Aryl-3-methoxycarbonyl-2,3-dihydrobenzofurans via the Rh(II)-Catalyzed C−H Insertion Process
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Catalytic asymmetric synthesis of 1,1′-spirobi[indan-3,3′-dione] via a double intramolecular C–H insertion process
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Enantioselective Synthesis of 4-Substituted 2-Pyrrolidinones by Site-selective C-H Insertion of α-Methoxycarbonyl-α-diazoacetanilides Catalyzed by Dirhodium(II) Tetrakis[N-phthaloyl-(S)-tert-leucinate]
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Highly enantioselective construction of the key azetidin-2-ones for the synthesis of carbapenem antibiotics via intramolecular C–H insertion reactions of α-methoxycarbonyl-α-diazoacetamides catalysed by chiral dirhodium() carboxylates
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Enantioselective Intramolecular C-H Insertion Reactions of α-Diazo β-Keto Esters Catalyzed by Dirhodium(II) Tetrakis[<i>N</i>-phthaloyl-(<i>S</i>)-phenylalaninate]: The Effect of the Substituent at the Insertion Site on Enantioselectivity
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Synthesis of Optically Active Ferrocene Analogues of Salicylic Acid Derivatives and Rhodium(II)-Catalyzed Asymmetric Intramolecular C–H Insertion of <i>α</i>-Diazo <i>β</i>-Keto Esters Using New Chiral Carboxylato Ligands
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(1R,5S)-(&amp;#8722;)-6,6-DIMETHYL-3-OXABICYCLO[3.1.0]HEXAN-2-ONE. HIGHLY ENANTIOSELECTIVE INTRAMOLECULAR CYCLOPROPANATION CATALYZED BY DIRHODIUM(II) TETRAKIS[METHYL 2-PYRROLIDONE-5(R)-CARBOXYLATE]
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Tetrakis[(4<i>S</i>)‐4‐phenyloxazolidin‐2‐one]dirhodium(II) and Its Catalytic Applications for Metal Carbene Transformations
resolves10.1002/recl.19951140407
Enhanced enantiocontrol in catalytic metal carbene transformations with dirhodium (II) tetrakis[methyl 2‐oxooxazolidin‐4(S)‐carboxylate], Rh<sub>2</sub>(4S‐MEOX)<sub>4</sub>
resolves10.1055/s-1996-5573
Dirhodium(II) Tetrakis[alkyl 2-oxaazetidine-4(S)-carboxylates]. A New Set of Effective Chiral Catalysts for Asymmetric Intermolecular Cyclopropanation Reactions with Diazoacetates
resolves10.1039/b001464h
Optimization of enantiocontrol in cis-selective cyclopropanation reactions catalyzed by dirhodium(ii) tetrakis[alkyl 2-oxaazetidine-4(S)-carboxylates]
resolves10.1021/jo015932f
High Selectivity from Configurational Match/Mismatch in Carbon−Hydrogen Insertion Reactions of Steroidal Diazoacetates Catalyzed by Chiral Dirhodium(II) Carboxamidates
resolves10.1016/S0040-4039(00)61106-1
A new rhodium(II) phosphate catalyst for diazocarbonyl reactions including asymmetric synthesis
resolves10.1016/S0040-4039(00)61107-3
Asymmetric dipolar cycloaddition reactions of diazocompounds mediated by a binaphtholphosphate rhodium catalyst
resolves10.1021/ja9819559
Synthesis, Structure, and Reactivity of the First Enantiomerically Pure Ortho-Metalated Rhodium(II) Dimer
resolves10.1021/om971070q
Reactivity and Selectivity of Ortho-Metalated Rhodium(II) Complexes in C−H Insertion Reactions of α-Diazo Compounds
resolves10.1016/S0022-328X(00)00357-0
ortho-Metalated dirhodium(II)-catalyzed α-diazocarbonyl transformation. Diastereoselective cyclopropanation of menthyl-α-diazo-β-keto ester and CH insertion of α-diazo ester
resolves10.1021/jo961607u
Intramolecular Regioselective Insertion into Unactivated Prochiral Carbon−Hydrogen Bonds with Diazoacetates of Primary Alcohols Catalyzed by Chiral Dirhodium(II) Carboxamidates. Highly Enantioselective Total Synthesis of Natural Lignan Lactones
resolves10.1021/ja00023a077
Asymmetric synthesis of lactones with high enantioselectivity by intramolecular carbon-hydrogen insertion reactions of alkyl diazoacetates catalyzed by chiral rhodium(II) carboxamides
resolves10.1021/jo00126a002
Optimization of Enantiocontrol for Carbon-Hydrogen Insertion with Chiral Dirhodium(II) Carboxamidates. Synthesis of Natural Dibenzylbutyrolactone Lignans from 3-Aryl-1-propyl Diazoacetates in High Optical Purity
resolves10.1021/jo016220s
Total Synthesis of (<i>S</i>)-(+)-Imperanene. Effective Use of Regio- and Enantioselective Intramolecular Carbon−Hydrogen Insertion Reactions Catalyzed by Chiral Dirhodium(II) Carboxamidates
resolves10.1002/1615-4169(200201)344:1<91::AID-ADSC91>3.0.CO;2-S
Highly Selective Synthesis of a 2-Deoxyxylonolactam via Enantioselective Carbon-Hydrogen Insertion Reactions Using Chiral Dirhodium(II) Carboxamidates
resolves10.1002/chir.10060
Enantioselective carbon‐‐hydrogen insertion is an effective and efficient methodology for the synthesis of (<b><i>r</i></b>)‐(‐)‐baclofen
resolves10.1021/ja961682m
Chiral Catalyst Controlled Diastereoselection and Regioselection in Intramolecular Carbon−Hydrogen Insertion Reactions of Diazoacetates
resolves10.1021/jo00049a010
Enantioselective metal carbene transformations with polyethylene-bound soluble recoverable dirhodium(II) 2-pyrrolidone-5(S)-carboxylates
resolves10.1016/S0040-4039(00)76684-6
Synthesis of 2-deoxyxylolactone from glycerol derivatives via highly enantioselective carbon-hydrogen insertion reactions
resolves10.1016/0040-4039(95)01561-U
Enhancement of enantiocontrol/diastereocontrol in catalytic intramolecular cyclopropanation and carbon-hydrogen insertion reactions of diazoacetates with Rh2(4S-MPPIM)4
resolves10.1021/jo991211t
Enantioselective Syntheses of 2-Deoxyxylono-1,4-lactone and 2-Deoxyribono-1,4-lactone from 1,3-Dioxan-5-yl Diazoacetates
resolves10.1021/ja00089a062
Diastereocontrol for Highly Enantioselective Carbon-Hydrogen Insertion Reactions of Cycloalkyl Diazoacetates
resolves10.1002/hlca.19940770307
Enantioselective Formation of Bicyclic Lactones by Rhodium‐Catalyzed Intramolecular CH‐insertion reactions
resolves10.1021/ja9945414
Enantiocontrolled Macrocycle Formation by Catalytic Intramolecular Cyclopropanation
resolves10.1016/S0040-4039(00)83988-X
A stereocontrolled route to optically active 1-methyl carbapenems
resolves10.1016/S0040-4039(00)74752-6
Enantiocontrol and regiocontrol in lactam syntheses by intramolecular carbon-hydrogen insertion reactions of diazoacetamides catalyzed by chiral rhodium(II) carboxamides
resolves10.1055/s-1995-5176
Highly Enantioselective Route to β-Lactams via Intramolecular C-H Insertion Reactions of Diazoacetylazacycloalkanes Catalyzed by Chiral Dirhodium(II) Carboxamidates
resolves10.1016/S0040-4039(01)02261-4
Synthesis of (±)-7-episordidin
resolves10.1007/BF02496127
Enantiocontrol in intramolecular cyclopropanation of diazoketones. Conformational control of metal carbene alignment
resolves10.1039/p19950000619
A new catalytic transformation of diazo esters: hydride abstraction in dirhodium(II)-catalysed reactions
resolves10.1021/jo990797g
Anomalous Products from Intramolecular C−H Insertion by a Rhodium Carbenoid. Possible Involvement of a Zwitterionic Mechanism
resolves10.1021/jo970842p
Anomalous Products from Intramolecular Insertion Reactions of Rhodium Carbenoids into the α-C−H Bonds of Ethers
resolves10.1016/S0040-4039(01)01173-X
Probing the mechanism of the anomalous intramolecular C–H insertion reaction of rhodium carbenoids by analysis of kinetic isotope effects
resolves10.1016/0040-4039(95)02252-X
Structure determination and synthesis of a new gibberellin, GA99, from spinach plants: 2β-hydroxy-GA19
resolves10.1080/00397919408010251
Double Asymmetric Induction in Intramolecular C-H Insertion Reactions of<i>α</i>-Diazo<i>β</i>-Keto Esters
resolves10.1016/S0040-4039(00)60689-5
Enhancement of enantioselectivity in intramolecular C-H insertion reactions of α-diazo β-keto esters catalyzed by chiral dirhodium(II) carboxylates
resolves10.1021/jo001519g
Synthesis of (−)-Astrogorgiadiol
resolves10.1055/s-1994-23075
Enantioselective Intramolecular C-H Insertion Reactions of<i>N</i>-Alkyl-<i>N</i>-<i>tert</i>-Butyl-α-Methoxycarbonyl-α-Diazoacetamides Catalyzed by Dirhodium(II) Carboxylates: Catalytic, Asymmetric Construction of 2-Azetidinones
resolves10.1016/0040-4039(95)02115-9
The Rh2(OAc)4 catalysed CH insertion in chiral ester diazoanilides
resolves10.3987/COM-99-8805
Studies on the Rh(II)-catalyzed C-H Insertion Reaction of Some Derivatives of N -[4-{(S)-1,2-Dihydroxy- butyl}]-a-diazoanilides: Site-Selectivity
resolves10.1055/s-1999-2958
Catalytic Enantioselective Synthesis of the Phosphodiesterase Type IV Inhibitor (<i>R</i>)-(-)-Rolipram <i>via</i> Intramolecular C-H Insertion Process
resolves10.1039/c39790000846
Preparation of 8-oxo-7-(1-hydroxyethyl)-3-oxa-1-azabicyclo[4.2.0]octane derivatives: intermediates for thienamycin synthesis
resolves10.1016/S0040-4039(98)02055-3
Enantioselective intramolecular CH insertion route to a key intermediate for the synthesis of trinem antibiotics
resolves10.3987/COM-99-S102
Double Stereodifferentiation in Intramolecular C-H Insertion Reaction toward the Synthesis of 1b-Methylcarbapenem Antibiotics
resolves10.1021/ol0157858
Asymmetric Intramolecular C−H Insertions of Aryldiazoacetates
resolves10.1016/S0040-4039(98)00836-3
Effect of carbenoid structure on the reactivity of rhodium-stabilized carbenoids
resolves10.1016/S0040-4020(00)00076-4
Intermolecular Cyclopropanation versus CH Insertion in RhII-Catalyzed Carbenoid Reactions
resolves10.1016/S0040-4020(01)91934-9
Transition metal catalyzed reactions of diazoesters
resolves10.1016/S0040-4039(00)00104-0
Effect of carbenoid structure on the reactions of rhodium-stabilized carbenoids with cycloheptatriene
resolves10.1021/ja0035607
Catalytic Asymmetric C−H Activation of Silyl Enol Ethers as an Equivalent of an Asymmetric Michael Reaction
resolves10.1021/ja016798j
Intermolecular Copper-Catalyzed Carbon−Hydrogen Bond Activation via Carbene Insertion
resolves10.1021/jo971910a
Rhodium-Catalyzed Insertion of Carbenoids into β C−H Bonds of Silacycloalkanes:  A Facile and General Approach to Functionalized Silacycloalkanes
resolves10.1021/ol0167255
Catalytic Asymmetric Allylic C−H Activation as a Surrogate of the Asymmetric Claisen Rearrangement
resolves10.1016/S0040-4039(02)00956-5
Catalytic asymmetric C–H activation by methyl thiophen-3-yldiazoacetate applied to the synthesis of (+)-cetiedil
resolves10.1021/ol9905699
Catalytic Asymmetric Synthesis of Diarylacetates and 4,4-Diarylbutanoates. A Formal Asymmetric Synthesis of (+)-Sertraline
resolves10.1016/S0040-4039(02)00941-3
Asymmetric synthesis of (+)-indatraline using rhodium-catalyzed C–H activation
resolves10.1021/jo016351t
Catalytic Asymmetric Benzylic C−H Activation by Means of Carbenoid-Induced C−H Insertions
resolves10.1016/S0957-4166(03)00154-X
Intermolecular C–H activation at benzylic positions: synthesis of (+)-imperanene and (−)-α-conidendrin
resolves10.1021/ja9910715
Highly Regio-, Diastereo-, and Enantioselective C−H Insertions of Methyl Aryldiazoacetates into Cyclic N-Boc-Protected Amines. Asymmetric Synthesis of Novel <i>C</i><sub>2</sub>-Symmetric Amines and <i>threo</i>-Methylphenidate
resolves10.1002/1521-3773(20020617)41:12<2197::AID-ANIE2197>3.0.CO;2-N
Catalytic Enantioselective Synthesis of β2-Amino Acids This work was supported by the National Science Foundation (CHE 0092490) and the National Institutes of Health (GM57425).
resolves10.1021/ol015974q
Kinetic Resolution and Double Stereodifferentiation in Catalytic Asymmetric C−H Activation of 2-Substituted Pyrrolidines
resolves10.1021/ol9905809
Catalytic Asymmetric Synthesis of<i>Syn</i>-Aldol Products from Intermolecular C−H Insertions between Allyl Silyl Ethers and Methyl Aryldiazoacetates
resolves10.1021/ol006671j
Asymmetric Catalytic C−H Activation Applied to the Synthesis of <i>Syn</i>-Aldol Products
resolves10.1016/S0040-4039(00)95992-6
Tandem cyclopropanation/Cope rearrangement sequence. Stereospecific [3 + 4] cycloaddition reaction of vinylcarbenoids with cyclopentadiene
resolves10.1016/0040-4039(88)85312-7
Novel approach to seven-membered rings by the intramolecular tandem cyclopropanation/cope rearrangement sequence
resolves10.1021/jo00265a037
Scope and stereochemistry of the tandem intramolecular cyclopropanation/Cope rearrangement sequence
resolves10.1021/jo00012a011
Stereoselective synthesis of seven-membered carbocycles by a tandem cyclopropanation/Cope rearrangement between rhodium(II)-stabilized vinylcarbenoids and dienes
resolves10.1021/ja974201n
Tandem Asymmetric Cyclopropanation/Cope Rearrangement. A Highly Diastereoselective and Enantioselective Method for the Construction of 1,4-Cycloheptadienes
resolves10.1021/ja016928o
A Stable Dirhodium Tetracarboxylate Carbenoid:  Crystal Structure, Bonding Analysis, and Catalysis
resolves10.1021/ja961806v
Saturation Kinetics in Dirhodium(II) Carboxylate-Catalyzed Decompositions of Diazo Compounds
resolves10.1016/0040-4020(89)80034-1
Kinetics of the dirhodium tetraacetate catalyzed decomposition of ethyl diazoacetate in 1,4-dioxane. Is nitrogen involved in the transition state?
resolves10.1021/jo9803434
Rhodium-Mediated Intramolecular C−H Insertion:  Probing the Geometry of the Transition State
resolves10.1021/jo0107352
A Kinetic Study on the Pairwise Competition Reaction of α-Diazo Esters with Rhodium(II) Catalysts:  Implication for the Mechanism of Rh(II)-Carbene Transfer
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