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H. Prokopcová, Sheba Bergman, Karel Aelvoet, Veerle Smout, W. Herrebout, B. Veken, L. Meerpoel, B. Maes (2010)
C-2 arylation of piperidines through directed transition-metal-catalyzed sp3 C-H activation.Chemistry, 16 44
C. Cardellicchio, M. Capozzi, F. Naso (2010)
The Betti base: the awakening of a sleeping beautyTetrahedron-asymmetry, 21
H. Iida, N. Yamazaki, C. Kibayashi, H. Nagase (1986)
Stereochemical revision and absolute configuration of codonopsinineTetrahedron Letters, 27
E. Severino, E. Costenaro, A. Garcia, C. Correia (2003)
Probing the stereoselectivity of the Heck arylation of endocyclic enecarbamates with diazonium salts. Concise syntheses of (2S,5R)-phenylproline methyl ester and Schramm's C-azanucleoside.Organic letters, 5 3
Hai‐Peng Bi, Liang Zhao, Yongping Liang, Chao‐Jun Li (2009)
The copper-catalyzed decarboxylative coupling of the sp3-hybridized carbon atoms of alpha-amino acids.Angewandte Chemie, 48 4
P. Wender, Mitchell Croatt, B. Witulski (2006)
New reactions and step economy: the total synthesis of (±)-salsolene oxide based on the type II transition metal-catalyzed intramolecular [4 + 4] cycloadditionTetrahedron, 62
Lei Shi, W. Xia (2012)
Photoredox functionalization of C-H bonds adjacent to a nitrogen atom.Chemical Society reviews, 41 23
G. Pandey, Prabal Banerjee, S. Gadre (2006)
Construction of enantiopure pyrrolidine ring system via asymmetric [3+2]-cycloaddition of azomethine ylides.Chemical reviews, 106 11
E. Corey, K. Achiwa (1969)
Oxidation of primary amines to ketonesJournal of the American Chemical Society, 91
J. Adrio, J. Carretero (2011)
Novel dipolarophiles and dipoles in the metal-catalyzed enantioselective 1,3-dipolar cycloaddition of azomethine ylides.Chemical communications, 47 24
K. Campos (2007)
Direct sp3 C-H bond activation adjacent to nitrogen in heterocycles.Chemical Society reviews, 36 7
F. Davis, Tianan Fang, R. Goswami (2002)
Asymmetric synthesis of substituted prolines from delta-amino beta-ketoesters. Methyl (2S,5R)-(+)-5-phenylpyrrolidine-2-carboxylate.Organic letters, 4 9
B. Trost (2002)
On inventing reactions for atom economy.Accounts of chemical research, 35 9
R. Guthrie, W. Meister, D. Cram (1967)
1,3-ASYMMETRIC INDUCTION IN A TRANSAMINATION REACTION.Journal of the American Chemical Society, 89
R. Miles, P. Tyler, G. Evans, R. Furneaux, D. Parkin, V. Schramm (1999)
Iminoribitol transition state analogue inhibitors of protozoan nucleoside hydrolases.Biochemistry, 38 40
C. Mannich, W. Krösche
Ueber ein Kondensationsprodukt aus Formaldehyd, Ammoniak und AntipyrinArchiv der Pharmazie, 250
N. Lin, G. Carrera, D. Anderson (1994)
Synthesis and evaluation of nicotine analogs as neuronal nicotinic acetylcholine receptor ligands.Journal of medicinal chemistry, 37 21
Anup Bhunia, S. Yetra, A. Biju (2012)
Recent advances in transition-metal-free carbon-carbon and carbon-heteroatom bond-forming reactions using arynes.Chemical Society reviews, 41 8
A. McNally, Christopher Prier, D. MacMillan (2011)
Discovery of an α-Amino C–H Arylation Reaction Using the Strategy of Accelerated SerendipityScience, 334
Kyungho Park, Yumi Heo, Sunwoo Lee (2013)
Metal-free decarboxylative three-component coupling reaction for the synthesis of propargylamines.Organic letters, 15 13
Chen Zhang, D. Seidel (2010)
Nontraditional reactions of azomethine ylides: decarboxylative three-component couplings of alpha-amino acids.Journal of the American Chemical Society, 132 6
M. Arend, B. Westermann, N. Risch (1998)
Moderne Varianten der Mannich‐ReaktionAngewandte Chemie, 110
S. Pastine, D. Gribkov, D. Sames (2006)
sp3 C-H bond arylation directed by amidine protecting group: alpha-arylation of pyrrolidines and piperidines.Journal of the American Chemical Society, 128 44
Zhao-Lin He, Huailong Teng, Chun‐Jiang Wang (2013)
Fulvenes as effective dipolarophiles in copper(I)-catalyzed [6+3] cycloaddition of azomethine ylides: asymmetric construction of piperidine derivatives.Angewandte Chemie, 52 10
F. Manfre, J. Pulicani (1994)
Enantiospecific synthesis and absolute configuration of (+)-RP 66803 a new non-peptide CCK antagonistTetrahedron-asymmetry, 5
M. Rueping, A. Parra (2010)
Fast, efficient, mild, and metal-free synthesis of pyrroles by domino reactions in water.Organic letters, 12 22
Timothy Newhouse, P. Baran, R. Hoffmann (2009)
The economies of synthesis.Chemical Society reviews, 38 11
P. Wender, B. Miller (2009)
Synthesis at the molecular frontierNature, 460
M. Arend, B. Westermann, N. Risch (1998)
Modern Variants of the Mannich Reaction.Angewandte Chemie, 37 8
Marcel Hartmann, Yi Li, A. Studer (2012)
Transition-metal-free oxyarylation of alkenes with aryl diazonium salts and TEMPONa.Journal of the American Chemical Society, 134 40
Deepankar Das, Aaron Sun, D. Seidel (2013)
Redox-neutral copper(II) carboxylate catalyzed α-alkynylation of amines.Angewandte Chemie, 52 13
K. Campos, Artis Klapars, Jacob Waldman, P. Dormer, Cheng-yi Chen (2006)
Enantioselective, Palladium-Catalyzed α-Arylation of N-Boc-pyrrolidineJournal of the American Chemical Society, 128
E. Mitchell, Aldo Peschiulli, Nicolas Lefèvre, L. Meerpoel, B. Maes (2012)
Direct α-functionalization of saturated cyclic amines.Chemistry, 18 33
Hai‐Peng Bi, Wen-Wen Chen, Yongping Liang, Chao‐Jun Li (2009)
A novel iron-catalyzed decarboxylative Csp3-Csp2 coupling of proline derivatives and naphthol.Organic letters, 11 15
B. Trost (1991)
The atom economy--a search for synthetic efficiency.Science, 254 5037
Pengfei Hu, Jianglei Hu, J. Jiao, Xiaofeng Tong (2013)
Amine-promoted asymmetric (4+2) annulations for the enantioselective synthesis of tetrahydropyridines: a traceless and recoverable auxiliary strategy.Angewandte Chemie, 52 20
Xiao Xiao, Ying Xie, C. Su, Mao Liu, Yian Shi (2011)
Organocatalytic asymmetric biomimetic transamination: from α-keto esters to optically active α-amino acid derivatives.Journal of the American Chemical Society, 133 33
S. Seel, Tobias Thaler, K. Takatsu, Cong Zhang, H. Zipse, B. Straub, P. Mayer, P. Knochel (2011)
Highly diastereoselective arylations of substituted piperidines.Journal of the American Chemical Society, 133 13
O. Diels, K. Alder
Synthesen in der hydroaromatischen ReiheEuropean Journal of Organic Chemistry, 460
C. Cimarelli, Davide Fratoni, A. Mazzanti, G. Palmieri (2011)
Betti Reaction of Cyclic Imines with Naphthols and Phenols – Preparation of New Derivatives of Betti's BasesEuropean Journal of Organic Chemistry, 2011
Noah Burns, Phil Baran, R. Hoffmann (2009)
Redoxkonomie in der organischen SyntheseAngewandte Chemie
T. Ono, V. Kukhar, V. Soloshonok (1996)
Biomimetic Reductive Amination of Fluoro Aldehydes and Ketones via [1,3]-Proton Shift Reaction.(1) Scope and Limitations.The Journal of organic chemistry, 61 19
N. Burns, P. Baran, R. Hoffmann (2009)
Redox economy in organic synthesis.Angewandte Chemie, 48 16
Sebastian Wertz, A. Studer (2013)
Nitroxide-catalyzed transition-metal-free aerobic oxidation processesGreen Chemistry, 15
N. Yoshikai, Adam Mieczkowski, A. Matsumoto, L. Ilies, E. Nakamura (2010)
Iron-catalyzed C-C bond formation at alpha-position of aliphatic amines via C-H bond activation through 1,5-hydrogen transfer.Journal of the American Chemical Society, 132 16
M. Haddad, Hassan Imogaı̈, M. Larchevěque (1998)
THE FIRST ENANTIOSELECTIVE SYNTHESIS OF THE CIS-2-CARBOXY-5-PHENYLPYRROLIDINEJournal of Organic Chemistry, 63
Longle Ma, Weijie Chen, D. Seidel (2012)
Redox-neutral α-cyanation of amines.Journal of the American Chemical Society, 134 37
Marco Potowski, J. Bauer, C. Strohmann, A. Antonchick, H. Waldmann (2012)
Highly enantioselective catalytic [6+3] cycloadditions of azomethine ylides.Angewandte Chemie, 51 38
I. Coldham, R. Hufton (2005)
Intramolecular dipolar cycloaddition reactions of azomethine ylides.Chemical reviews, 105 7
S. Mukherjee, J. Yang, S. Hoffmann, B. List (2007)
Asymmetric enamine catalysis.Chemical reviews, 107 12
Arylated aliphatic N‐heterocycles, and particularly arylated pyrrolidines, have a wide range of applications in medicine as well as in chemistry. Arylation of pyrrolidines mainly relies on metal‐mediated couplings, which produce unwanted toxic metal waste. In this Communication, we report an oxidant‐ and metal‐free method for direct sp3 CH arylation of pyrrolidine employing a highly atom economic three‐component reaction. The method, operating under very simple and mild conditions, is highly selective and very efficient in producing single regioisomer of the arylated product even on a multigram scale. As an alternative to the metal‐mediated reaction, this method has the potential to be used in production at an industrial scale. Moreover, a new approach for CH arylation based on a novel reactivity that differs from the reactivity in Mannich or Betti reactions of iminium ion is presented.
Asian Journal of Organic Chemistry – Wiley
Published: Jan 1, 2014
Keywords: ; ; ; ;
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