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C-H Functionalization In The Synthesis Of Amino Acids And Peptides.

Anaïs F. M. Noisier, M. Brimble
Published 2014 · Chemistry, Medicine

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10.1021/CR020049I
New chiral phosphorus ligands for enantioselective hydrogenation.
Wenjun Tang (2003)
10.1002/anie.201003544
Palladium-catalyzed β arylation of carboxylic esters.
Alice Renaudat (2010)
10.1002/anie.200806273
Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality.
X. Chen (2009)
10.1126/SCIENCE.280.5363.560
Platinum catalysts for the high-yield oxidation of methane to a methanol derivative
Periana (1998)
10.1002/anie.201301451
Catalytic functionalization of C(sp2)-H and C(sp3)-H bonds by using bidentate directing groups.
Guy Rouquet (2013)
10.1039/c3cc48481e
A mild and selective Pd-mediated methodology for the synthesis of highly fluorescent 2-arylated tryptophans and tryptophan-containing peptides: a catalytic role for Pd(0) nanoparticles?
T. J. Williams (2014)
10.1002/anie.201310000
Direct borylation of primary C-H bonds in functionalized molecules by palladium catalysis.
L. Zhang (2014)
10.1021/jo401510b
Enantioselective synthesis of 2-substitued-tetrahydroisoquinolin-1-yl glycine derivatives via oxidative cross-dehydrogenative coupling of tertiary amines and chiral nickel(II) glycinate.
Shengbin Zhou (2013)
10.1021/OL061389J
Novel acetoxylation and C-C coupling reactions at unactivated positions in alpha-amino acid derivatives.
B. S. Reddy (2006)
10.1002/anie.200903671
High-oxidation-state palladium catalysis: new reactivity for organic synthesis.
K. Muñiz (2009)
10.1016/j.bmc.2012.02.035
Tyrosine modified analogues of the α4β7 integrin inhibitor biotin-R₈ERY prepared via Click Chemistry: synthesis and biological evaluation.
Stefanie Papst (2012)
10.1021/JA020290E
Synthesis of novel quaternary amino acids using molybdenum-catalyzed asymmetric allylic alkylation.
B. Trost (2002)
10.1246/CL.2010.1118
Overview of the Mechanistic Work on the Concerted Metallation-Deprotonation Pathway
D. Lapointe (2010)
10.1021/ol1015674
Functionalization of aromatic amino acids via direct C-H activation: generation of versatile building blocks for accessing novel peptide space.
Falco-Magnus Meyer (2010)
10.1021/OL035178F
Synthesis of a TMC-95A ketomethylene analogue by cyclization via intramolecular Suzuki coupling.
M. Kaiser (2003)
10.1021/ol1007108
Pd(II)-catalyzed o-C-H acetoxylation of phenylalanine and ephedrine derivatives with MeCOOO(t)Bu/Ac2O.
Chris J. Vickers (2010)
10.1002/chem.200902676
Postsynthetic modification of peptides: chemoselective C-arylation of tryptophan residues.
Javier Ruíz-Rodríguez (2010)
10.1021/ja906935c
Bimetallic palladium catalysis: direct observation of Pd(III)-Pd(III) intermediates.
D. C. Powers (2009)
10.1002/1521-3773(20020816)41:16<3056::AID-ANIE3056>3.0.CO;2-#
A stoichiometric aromatic CbondH borylation catalyzed by iridium(i)/2,2'-bipyridine complexes at room temperature.
T. Ishiyama (2002)
10.1039/c0cs00182a
C-H functionalization logic in total synthesis.
W. R. Gutekunst (2011)
10.1002/anie.201206237
Synthesis of aromatic α-aminoesters: palladium-catalyzed long-range arylation of primary C sp 3-H bonds.
Sam Aspin (2012)
10.1002/anie.201306181
Iron-catalyzed oxidative C-H/C-H cross-coupling: an efficient route to α-quaternary α-amino acid derivatives.
K. Li (2013)
10.1039/c1cs15058h
Transition metal-catalyzed arylation of unactivated C(sp3)-H bonds.
O. Baudoin (2011)
10.1002/chem.201101340
Rh(III)-catalyzed oxidative olefination of vinylic C-H bonds: efficient and selective access to di-unsaturated α-amino acid derivatives and other linear 1,3-butadienes.
Tatiana Besset (2011)
10.1021/cr900279a
Cyclometalation using d-block transition metals: fundamental aspects and recent trends.
M. Albrecht (2010)
10.1016/j.drudis.2013.05.011
Future directions for peptide therapeutics development.
Allan A. Kaspar (2013)
10.1021/CR020038P
Catalytic enantioselective Strecker reactions and analogous syntheses.
H. Gröger (2003)
10.1039/B103832J
Direct synthesis of Fmoc-protected amino acids using organozinc chemistry: application to polymethoxylated phenylalanines and 4-oxoamino acids
H. J. C. Deboves (2001)
10.1021/JA067144J
Palladium-catalyzed benzene arylation: incorporation of catalytic pivalic acid as a proton shuttle and a key element in catalyst design.
M. Lafrance (2006)
10.1021/cr9000836
Transition metal-catalyzed direct arylation of substrates with activated sp3-hybridized C-H bonds and some of their synthetic equivalents with aryl halides and pseudohalides.
F. Bellina (2010)
10.1021/ar800164n
Cross-dehydrogenative coupling (CDC): exploring C-C bond formations beyond functional group transformations.
C. Li (2009)
10.1038/nature06485
Catalytic C–H functionalization by metal carbenoid and nitrenoid insertion
H. Davies (2008)
10.1021/cr900206p
C-H activation for the construction of C-B bonds.
I. Mkhalid (2010)
10.1002/anie.201100984
A practical strategy for the structural diversification of aliphatic scaffolds through the palladium-catalyzed picolinamide-directed remote functionalization of unactivated C(sp3)-H bonds.
Gang He (2011)
10.1039/C2SC21162A
Palladium-catalyzed N-(2-pyridyl)sulfonyl-directed C(sp3)–H γ-arylation of amino acid derivatives
Nuria Rodríguez (2013)
10.1002/EJOC.201101656
An Efficient Route to Quinolines and Other Compounds by Iron‐Catalysed Cross‐Dehydrogenative Coupling Reactions of Glycine Derivatives
P. Liu (2012)
10.1021/JA053433G
Mechanism of the mild functionalization of arenes by diboron reagents catalyzed by iridium complexes. Intermediacy and chemistry of bipyridine-ligated iridium trisboryl complexes.
Timothy M Boller (2005)
10.1002/EJOC.200900599
Peptidomimetics – A Versatile Route to Biologically Active Compounds
Andreas A Grauer (2009)
10.1021/CR0509760
Aryl-aryl bond formation by transition-metal-catalyzed direct arylation.
Dino Alberico (2007)
10.1021/JA016032J
Palladium-Catalyzed α-Arylation of Esters and Protected Amino Acids
S. Lee (2001)
10.1016/S0040-4039(00)90648-8
Aromatic substitution of styrene-palladium chloride complex
Ichiro Moritanl (1967)
10.1021/ol201865h
Pd-catalyzed C4-olefination of oxazoles via C-H bond activation: divergent synthesis of functionalized amino alcohol and amino acid derivatives.
S. Cui (2011)
10.1021/jo401934q
Palladium-catalyzed regioselective C-5 arylation of protected L-histidine: microwave-assisted C-H activation adjacent to donor arm.
Amit Mahindra (2013)
10.1002/anie.201306625
Stereoselective synthesis of chiral α-amino-β-lactams through palladium(II)-catalyzed sequential monoarylation/amidation of C(sp(3) )-H bonds.
Q. Zhang (2013)
10.1021/cr200057t
Asymmetric strecker reactions.
J. Wang (2011)
10.1021/JA061715Q
Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant.
X. Chen (2006)
10.1021/ja301461p
Benzylic phosphates as electrophiles in the palladium-catalyzed asymmetric benzylation of azlactones.
B. Trost (2012)
10.1021/cr100412j
Carboxylate-assisted transition-metal-catalyzed C-H bond functionalizations: mechanism and scope.
L. Ackermann (2011)
10.1002/anie.201004940
Cross-dehydrogenative coupling reactions by transition-metal and aminocatalysis for the synthesis of amino acid derivatives.
J. Xie (2010)
10.1021/JA054549F
Highly regioselective arylation of sp3 C-H bonds catalyzed by palladium acetate.
V. Zaitsev (2005)
10.1021/jo901744y
Synthesis of a cyclic pentapeptide mimic of the active site His-Tyr cofactor of cytochrome c oxidase.
Maximillian E. Mahoney (2009)
10.1111/cbdd.12055
The Future of Peptide‐based Drugs
D. Craik (2013)
10.1002/ANIE.200502767
Pd-catalyzed stereoselective oxidation of methyl groups by inexpensive oxidants under mild conditions: a dual role for carboxylic anhydrides in catalytic C--H bond oxidation.
R. Giri (2005)
10.1002/anie.200905134
Total synthesis of celogentin C by stereoselective C-H activation.
Y. Feng (2010)
10.1002/1521-3773(20020617)41:12<2197::AID-ANIE2197>3.0.CO;2-N
Catalytic Enantioselective Synthesis of 2-Amino Acids.
H. Davies (2002)
10.1002/1099-0690(200008)2000:15<2689::AID-EJOC2689>3.0.CO;2-T
Glycine and Alanine Imines as Templates for Asymmetric Synthesis of α‐Amino Acids
T. Abellan (2000)
10.1021/OL051255Q
Catalytic coupling of C-H and C-I bonds using pyridine as a directing group.
D. Shabashov (2005)
10.1021/jo400961x
Synthesis of C-2 arylated tryptophan amino acids and related compounds through palladium-catalyzed C-H activation.
S. Preciado (2013)
10.1021/ja312277g
Palladium-catalyzed picolinamide-directed alkylation of unactivated C(sp3)-H bonds with alkyl iodides.
S. Zhang (2013)
10.1021/CR068368N
Recent development and application of chiral phase-transfer catalysts.
T. Hashimoto (2007)
10.1021/OL034570Q
Palladium-Catalyzed α-Arylation of Azlactones to Form Quaternary Amino Acid Derivatives
X. Liu (2003)
10.1021/AR0300625
The enantioselective synthesis of alpha-amino acids by phase-transfer catalysis with achiral Schiff base esters.
M. O'Donnell (2004)
10.1002/anie.201304268
The cross-dehydrogenative coupling of C(sp3)-H bonds: a versatile strategy for C-C bond formations.
Simon A. Girard (2014)
10.1073/pnas.0809052106
Site-specific C-functionalization of free-(NH) peptides and glycine derivatives via direct C–H bond functionalization
L. Zhao (2009)
10.1002/anie.201105123
Catalytic asymmetric activation of a C(sp³)-H bond adjacent to a nitrogen atom: a versatile approach to optically active α-alkyl α-amino acids and C1-alkylated tetrahydroisoquinoline derivatives.
G. Zhang (2011)
10.1021/JA00365A091
Carbon-hydrogen activation in completely saturated hydrocarbons: direct observation of M + R-H .fwdarw. M(R)(H)
Andrew H. Janowicz (1982)
10.1002/anie.201306583
Palladium-catalyzed direct functionalization of 2-aminobutanoic acid derivatives: application of a convenient and versatile auxiliary.
M. Fan (2013)
10.1021/JO0606913
Controlled synthesis of (S,S)-2,7-diaminosuberic acid: a method for regioselective construction of dicarba analogues of multicystine-containing peptides.
Jomana Elaridi (2006)
10.1039/C3SC51747K
Pd(II)-catalyzed alkylation of unactivated C(sp3)–H bonds: efficient synthesis of optically active unnatural α-amino acids
Kai Chen (2013)
10.1002/ADSC.200390000
Selective Hydrogenation for Fine Chemicals: Recent Trends and New Developments
H. Blaser (2003)
10.1021/ja406484v
Stereoselective synthesis of β-alkylated α-amino acids via palladium-catalyzed alkylation of unactivated methylene C(sp3)-H bonds with primary alkyl halides.
S. Zhang (2013)
10.1002/anie.201201666
C-H bond functionalization: emerging synthetic tools for natural products and pharmaceuticals.
J. Yamaguchi (2012)
10.1021/JA060809X
Room temperature palladium-catalyzed 2-arylation of indoles.
Nicholas R. Deprez (2006)
10.1021/ja904116k
Synthetic and mechanistic studies of Pd-catalyzed C-H arylation with diaryliodonium salts: evidence for a bimetallic high oxidation state Pd intermediate.
Nicholas R. Deprez (2009)
10.1021/cr100280d
Catalytic dehydrogenative cross-coupling: forming carbon-carbon bonds by oxidizing two carbon-hydrogen bonds.
C. Yeung (2011)
10.1021/cr900184e
Palladium-catalyzed ligand-directed C-H functionalization reactions.
T. W. Lyons (2010)
10.1039/B711533D
Site-selective modification of peptides using rhodium and palladium catalysis: complementary electrophilic and nucleophilic arylation.
C. J. Chapman (2007)
10.1021/ja802533u
Analysis of the concerted metalation-deprotonation mechanism in palladium-catalyzed direct arylation across a broad range of aromatic substrates.
S. Gorelsky (2008)
10.1039/C39850000171
Preparation of optically pure α-methyl-α-amino acids via alkylation of the nickel(II) Schiff base of (R,S)-alanine with (S)-2-N-(N′-benzylprolyl)aminobenzaldehyde
Yuri N. Belokon (1985)
10.1002/anie.200801367
Functionalizing glycine derivatives by direct C-C bond formation.
L. Zhao (2008)
10.1039/c2cc36962a
Peptidic macrocyclization via palladium-catalyzed chemoselective indole C-2 arylation.
Huijun Dong (2012)
10.1039/B606984N
Direct transition metal-catalyzed functionalization of heteroaromatic compounds.
I. V. Seregin (2007)
10.1021/jo100693m
Low-valent iron-catalyzed C-C bond formation-addition, substitution, and C-H bond activation.
E. Nakamura (2010)
10.1002/ANIE.199726351
Catalytic Asymmetric Alkylation of Nucleophiles: Asymmetric Synthesis of α‐Alkylated Amino Acids
B. Trost (1997)
10.1039/B906119C
The catalytic ortho-arylation of tyrosine
R. Bedford (2009)
10.1016/J.TET.2005.11.027
Transition metal catalyzed oxidative functionalization of carbon-hydrogen bonds
A. Dick (2006)
10.1126/SCIENCE.1114731
C-H Bond Functionalization in Complex Organic Synthesis
Kamil Godula (2006)
10.1021/ja00377a032
Oxidative addition of the carbon-hydrogen bonds of neopentane and cyclohexane to a photochemically generated iridium(I) complex
J. Hoyano (1982)
10.1021/jo901822b
Boc groups as protectors and directors for Ir-catalyzed C-H borylation of heterocycles.
Venkata A. Kallepalli (2009)
10.1002/anie.200802187
Synthesis of indolines and tetrahydroisoquinolines from arylethylamines by Pd(II)-catalyzed C-H activation reactions.
J. Li (2008)
10.1039/c3cc44717k
Novel preparation of chiral α-amino acids using the Mitsunobu-Tsunoda reaction.
Anais F. M. Noisier (2013)
10.1002/chem.201201329
C-H activation: a complementary tool in the total synthesis of complex natural products.
D. Y. Chen (2012)
10.1021/JO051076M
Synthesis of the side chain cross-linked tyrosine oligomers dityrosine, trityrosine, and pulcherosine.
Ojia Skaff (2005)
10.1126/SCIENCE.1067074
Remarkably Selective Iridium Catalysts for the Elaboration of Aromatic C-H Bonds
Jian-Yang Cho (2001)
10.1002/chem.200902374
Functionalization of organic molecules by transition-metal-catalyzed C(sp3)-H activation.
Rodolphe Jazzar (2010)
10.1002/asia.201300990
Palladium-catalyzed cross-dehydrogenative functionalization of C(sp(2))-H Bonds.
Yinuo Wu (2014)
10.1038/417507a
Understanding and exploiting C–H bond activation
J. Labinger (2002)
10.1002/anie.201200731
Nonnatural amino acid synthesis by using carbon-hydrogen bond functionalization methodology.
L. D. Tran (2012)
10.1002/ANIE.200390037
The catalytic intermolecular orthoarylation of phenols.
R. Bedford (2003)
10.1038/446391a
Organometallic chemistry: C–H activation
R. Bergman (2007)
10.1002/ANIE.200462884
Palladium-catalyzed asymmetric iodination of unactivated C-H bonds under mild conditions.
R. Giri (2005)



This paper is referenced by
10.1039/c5ob02515j
Synthesis of substituted benzo[ij]imidazo[2,1,5-de]quinolizine by rhodium(III)-catalyzed multiple C-H activation and annulations.
Qingmei Ge (2016)
10.1021/ACS.ORGANOMET.6B00201
Synthesis of Quinoline-Based NNN-Pincer Nickel(II) Complexes: A Robust and Improved Catalyst System for C–H Bond Alkylation of Azoles with Alkyl Halides
Ulhas N. Patel (2016)
10.1039/c9np00075e
Harnessing the biocatalytic potential of iron- and α-ketoglutarate-dependent dioxygenases in natural product total synthesis.
Christian R. Zwick (2020)
10.1002/CHIN.201445270
C—H Functionalization in the Synthesis of Amino Acids and Peptides
Anais F. M. Noisier (2014)
10.1021/acs.orglett.5b03462
Ir(III)-Catalyzed Synthesis of Isoquinoline N-Oxides from Aryloxime and α-Diazocarbonyl Compounds.
R. Phatake (2016)
10.1002/AJOC.201700442
CuI/I2‐Mediated Intramolecular Oxidative Cyclization Reaction of N‐(2‐pyridyl)amidines by the Direct Double C−H Functionalization of a C(sp3)−H Bond
Fengping Yi (2017)
10.1039/C9GC00755E
Glycerol conversion to high-value chemicals: the implication of unnatural α-amino acid syntheses using natural resources
Yun Ji Park (2019)
10.1016/j.mencom.2020.07.038
The effect of N-substituent on the relative thermodynamic stability of unionized and zwitterionic forms of α-diphenylphosphino-α-amino acids
O. S. Soficheva (2020)
10.1016/J.TET.2017.01.060
The regioselective C5 halogenation of quinolines using sodium halides under transition metal-free conditions
Jun-Ying Jiao (2017)
10.1002/9783527810857.ch4
Substrate‐Controlled Transformation: Diastereoselective Functionalization
Shengyi Yan (2019)
10.1002/asia.201500599
Mechanism of Nickel(II)-Catalyzed Oxidative C(sp²)-H/C(sp³)-H Coupling of Benzamides and Toluene Derivatives.
Zheng-Yang Xu (2015)
10.1002/adsc.201700626
Combining Sanford Arylations on Benzodiazepines with the Nuisance Effect
Raysa Khan (2017)
10.1021/acscatal.6b03121
Mild and Regioselective Pd(OAc)2-Catalyzed C–H Arylation of Tryptophans by [ArN2]X, Promoted by Tosic Acid
A. Reay (2017)
10.1002/anie.201806963
A General Approach to Site-Specific, Intramolecular C-H Functionalization Using Dithiocarbamates.
Christina G Na (2018)
10.1021/ACSCATAL.6B01774
Functionalized Polymer-Supported Pyridine Ligands for Palladium-Catalyzed C(sp3)–H Arylation
Li-Chen Lee (2016)
10.1002/anie.202007226
Late-Stage Peptide Macrocyclization via Palladium-Catalyzed Site-selective C-H Olefination of Tryptophan.
Zengbing Bai (2020)
10.1002/ANGE.202002258
Mechanistische Studien zu Cobalta(III/IV/II)‐Elektrokatalyse: Oxidativ‐induzierte reduktive Eliminierung zur zweifachen C‐H‐Aktivierung
Tjark H Meyer (2020)
10.1002/APP.47597
Introduction of two polyvinyl alcohol resins for efficient solid support Cu‐catalyzed N‐arylation of α‐aminoacids with aryl halides in aqueous media
M. Kazemnejadi (2019)
10.1016/J.CCLET.2015.12.021
Synthesis of unnatural amino acids through palladium-catalyzed C(sp 3 )-H functionalization
Xi Lu (2016)
10.1016/J.POLY.2017.04.014
3-Phenylphosphaprolines – Synthesis, structure and properties of heterocyclic α-phosphanyl amino acids
Kaleswara R. Basvani (2017)
10.1002/EJOC.201700562
Influence of Base Strength on the Proton‐Transfer Reaction by Density Functional Theory
Binfang Yuan (2017)
10.1039/C6TA08335H
Nitrogen, phosphorus and sulfur co-doped ultrathin carbon nanosheets as a metal-free catalyst for selective oxidation of aromatic alkanes and the oxygen reduction reaction
Y. Zhu (2016)
10.1021/acs.orglett.6b01857
Visible-Light-Promoted Dual C-C Bond Formations of Alkynoates via a Domino Radical Addition/Cyclization Reaction: A Synthesis of Coumarins.
Shangbiao Feng (2016)
10.1002/9783527691920.CH6
Rh‐Catalyzed Synthesis of Oxygen‐Containing Heterocycles
Bin Liu (2016)
10.1021/ACSCATAL.6B01987
Palladium-Catalyzed Carbonylative Cyclization of Amines via γ-C(sp3)-H Activation: Late-Stage Diversification of Amino Acids and Peptides
Elier Hernando (2016)
10.1039/c9cs00366e
Peptide macrocyclization by transition metal catalysis.
Daniel G Rivera (2020)
10.1038/s41557-018-0087-7
Design of catalysts for site-selective and enantioselective functionalization of non-activated primary C–H bonds
Kuangbiao Liao (2018)
10.1039/c8ob00035b
Understanding the conformational analysis of gababutin based hybrid peptides.
Maruthi Konda (2018)
10.1021/acs.joc.7b00535
Pd(II)-Catalyzed, Picolinamide-Assisted, Z-Selective γ-Arylation of Allylamines To Construct Z-Cinnamylamines.
Ramarao Parella (2017)
10.1016/J.MOLCATA.2016.06.026
Ru-catalyzed C-H functionalization of phenylglycine derivatives: Synthesis of isoquinoline-1-carboxylates and isoindoline-1-carboxylates
S. Ruíz (2017)
10.1002/chem.201903756
Late‐Stage Diversification of Tryptophan‐Derived Biomolecules
H. Gruß (2019)
10.1002/anie.201607766
Divergent and Stereoselective Synthesis of β-Silyl-α-Amino Acids through Palladium-Catalyzed Intermolecular Silylation of Unactivated Primary and Secondary C-H Bonds.
Yuejin Liu (2016)
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