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Search for "organocatalysis" in Full Text gives 193 result(s) in Beilstein Journal of Organic Chemistry.

Copper-catalyzed asymmetric sp3 C–H arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalyst

  • Pierre Querard,
  • Inna Perepichka,
  • Eli Zysman-Colman and
  • Chao-Jun Li

Beilstein J. Org. Chem. 2016, 12, 2636–2643, doi:10.3762/bjoc.12.260

Graphical Abstract
  • of THIQs with arylboronic esters via asymmetric organocatalysis methodology [25][28]. The use of chiral tartaric acid derivatives, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and high temperature (70 °C) were found to be the optimal conditions to obtain the desired arylated product with
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Published 06 Dec 2016

Towards the development of continuous, organocatalytic, and stereoselective reactions in deep eutectic solvents

  • Davide Brenna,
  • Elisabetta Massolo,
  • Alessandra Puglisi,
  • Sergio Rossi,
  • Giuseppe Celentano,
  • Maurizio Benaglia and
  • Vito Capriati

Beilstein J. Org. Chem. 2016, 12, 2620–2626, doi:10.3762/bjoc.12.258

Graphical Abstract
  • . Keywords: continuous process; DES; organocatalysis; proline; stereoselective aldol reaction; Introduction The aldol reaction is a powerful synthetic tool to create new C–C bonds [1]. It offers several possibilities to control the stereochemical outcome of the process and to afford stereochemically defined
  • when using an apparently simple organocatalyst such as L-proline. These observations have important implications in the future design of chiral catalysts, thereby opening the floodgates to new intriguing opportunities for organocatalysis in unconventional reaction media. Experimental set-up I: test
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Published 05 Dec 2016

Highly chemo-, enantio-, and diastereoselective [4 + 2] cycloaddition of 5H-thiazol-4-ones with N-itaconimides

  • Shuai Qiu,
  • Choon-Hong Tan and
  • Zhiyong Jiang

Beilstein J. Org. Chem. 2016, 12, 2293–2297, doi:10.3762/bjoc.12.222

Graphical Abstract
  • ) were obtained for a series of spirocyclic 1,4-sulfur-bridged piperidinone-based succinimides. Keywords: [4 + 2] annulation; asymmetric organocatalysis; dipeptide-based Brønsted bases; 5H-thiazol-4-ones; N-itaconimides; Introduction Sulfur-containing tetrasubstituted carbon stereocenters are widely
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Published 01 Nov 2016

Correction: Recent advances in N-heterocyclic carbene (NHC)-catalysed benzoin reactions

  • Rajeev S. Menon,
  • Akkattu T. Biju and
  • Vijay Nair

Beilstein J. Org. Chem. 2016, 12, 2124–2124, doi:10.3762/bjoc.12.201

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  • Interdisciplinary Science and Technology,Trivandrum 695 019, India.; Fax: +91 471 2491712; Tel: +91 471 2490406 10.3762/bjoc.12.201 Keywords: acyloin reaction; benzoin reaction; N-heterocyclic carbenes; organocatalysis; umpolung; On page 446, column 2, the sentence “Inoue and co-workers found that it promotes
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Published 04 Oct 2016

Chiral ammonium betaine-catalyzed asymmetric Mannich-type reaction of oxindoles

  • Masahiro Torii,
  • Kohsuke Kato,
  • Daisuke Uraguchi and
  • Takashi Ooi

Beilstein J. Org. Chem. 2016, 12, 2099–2103, doi:10.3762/bjoc.12.199

Graphical Abstract
  • quaternary and tertiary stereogenic carbon centers on biologically intriguing molecular frameworks with high fidelity. Keywords: ammonium betaine; asymmetric catalysis; Mannich reaction; organocatalysis; oxindole; Introduction Chiral indole alkaloids possessing C-3 quaternary indoline frameworks are an
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Published 28 Sep 2016

Economical and scalable synthesis of 6-amino-2-cyanobenzothiazole

  • Jacob R. Hauser,
  • Hester A. Beard,
  • Mary E. Bayana,
  • Katherine E. Jolley,
  • Stuart L. Warriner and
  • Robin S. Bon

Beilstein J. Org. Chem. 2016, 12, 2019–2025, doi:10.3762/bjoc.12.189

Graphical Abstract
  • -cyanobenzothiazoles; DABCO; luciferins; organocatalysis; Introduction Functionalised 2-cyanobenzothiazoles (CBTs, 1) are key building blocks for the synthesis of luciferins 3 [1][2][3], substrates of natural and engineered firefly luciferases that are widely used for bioluminescence imaging (BLI) [4][5]. The typical
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Published 13 Sep 2016

Ionic liquids as transesterification catalysts: applications for the synthesis of linear and cyclic organic carbonates

  • Maurizio Selva,
  • Alvise Perosa,
  • Sandro Guidi and
  • Lisa Cattelan

Beilstein J. Org. Chem. 2016, 12, 1911–1924, doi:10.3762/bjoc.12.181

Graphical Abstract
  • therapeutics, imaging agents and packaging films and coatings [77]. Conclusion The literature survey illustrated in this review highlights three main facts. Firstly, organocatalysis by ionic liquids can be an efficient tool for base and even acid-catalyzed transesterification reactions in place of traditional
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Published 26 Aug 2016

Rearrangements of organic peroxides and related processes

  • Ivan A. Yaremenko,
  • Vera A. Vil’,
  • Dmitry V. Demchuk and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2016, 12, 1647–1748, doi:10.3762/bjoc.12.162

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Published 03 Aug 2016

Enantioselective addition of diphenyl phosphonate to ketimines derived from isatins catalyzed by binaphthyl-modified organocatalysts

  • Hee Seung Jang,
  • Yubin Kim and
  • Dae Young Kim

Beilstein J. Org. Chem. 2016, 12, 1551–1556, doi:10.3762/bjoc.12.149

Graphical Abstract
  • organocatalyst; ketimines; organocatalysis; squaramide; Introduction α-Aminophosphonate derivatives are important compounds as structural mimics of natural α-amino acids [1][2][3]. Chiral α-aminophosphonates have been shown a wide range of biological activities including antibacterial [4] and anticancer
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Published 20 Jul 2016

Catalytic asymmetric synthesis of biologically important 3-hydroxyoxindoles: an update

  • Bin Yu,
  • Hui Xing,
  • De-Quan Yu and
  • Hong-Min Liu

Beilstein J. Org. Chem. 2016, 12, 1000–1039, doi:10.3762/bjoc.12.98

Graphical Abstract
  • , enantioenriched 3-hydroxyoxindole scaffolds also exist in natural products and have proven to possess promising biological activities. A large number of catalytic asymmetric strategies toward the construction of 3-hydroxyoxindoles based on transition metal catalysis and organocatalysis have been reported in the
  • -substituted 3-hydroxyoxindoles and 3-hydroxyoxindole-based further transformations. Keywords: 3-hydroxyoxindoles; oxindoles; organocatalysis; spirooxindoles; transition metal catalysis; Introduction Chiral oxindoles are an important class of compounds, which widely exist in nature and have exhibited diverse
  • excellent ee values (up to 97% ee) from DMTr (Di(p-methoxyphenyl)phenylmethyl)-N-protected isatins in one-pot under modified conditions. Organocatalyzed synthesis of 3-substituted 3-hydroxyoxindoles Organocatalysis has witnessed significant progress in the last decades, a large number of new organocatalysts
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Published 18 May 2016

1H-Imidazol-4(5H)-ones and thiazol-4(5H)-ones as emerging pronucleophiles in asymmetric catalysis

  • Antonia Mielgo and
  • Claudio Palomo

Beilstein J. Org. Chem. 2016, 12, 918–936, doi:10.3762/bjoc.12.90

Graphical Abstract
  • efficient platforms for bidentate coordination in metal catalysis and good precursors of carboxylic acids, ketones and aldehydes upon oxidative cleavage of the keto/diol moiety [72]. More recently, a comprehensive study on the first evidence of the utility of these acceptors in organocatalysis has been
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Published 09 May 2016

Asymmetric α-amination of 3-substituted oxindoles using chiral bifunctional phosphine catalysts

  • Qiao-Wen Jin,
  • Zhuo Chai,
  • You-Ming Huang,
  • Gang Zou and
  • Gang Zhao

Beilstein J. Org. Chem. 2016, 12, 725–731, doi:10.3762/bjoc.12.72

Graphical Abstract
  • organocatalysis and metal catalysis for the construction of this type of structures. For example, Chen et al. reported the first organocatalytic enantioselective amination reaction of 2-oxindoles catalyzed by biscinchona alkaloid catalysts [8]. Zhou [9][10] and Barbas [11][12], have independently reported similar
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Published 15 Apr 2016

Stereoselective amine-thiourea-catalysed sulfa-Michael/nitroaldol cascade approach to 3,4,5-substituted tetrahydrothiophenes bearing a quaternary stereocenter

  • Sara Meninno,
  • Chiara Volpe,
  • Giorgio Della Sala,
  • Amedeo Capobianco and
  • Alessandra Lattanzi

Beilstein J. Org. Chem. 2016, 12, 643–647, doi:10.3762/bjoc.12.63

Graphical Abstract
  • affording the heterocyclic products in good yields and moderate stereoselectivities. Keywords: cascade reaction; tetrahydrothiophenes; aymmetric synthesis; amine thioureas; organocatalysis; Introduction The interest toward the development of stereoselective methodologies to prepare tetrahydrothiophenes
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Published 05 Apr 2016

Supported bifunctional thioureas as recoverable and reusable catalysts for enantioselective nitro-Michael reactions

  • José M. Andrés,
  • Miriam Ceballos,
  • Alicia Maestro,
  • Isabel Sanz and
  • Rafael Pedrosa

Beilstein J. Org. Chem. 2016, 12, 628–635, doi:10.3762/bjoc.12.61

Graphical Abstract
  • the thiourea derived from (L)-valine and 1,6-hexanediamine. The catalysts can be used in only 2 mol % loading, and reused for at least four cycles in neat conditions. The ball milling promoted additions also worked very well. Keywords: bifunctional organocatalysts; organocatalysis; stereoselective
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Published 01 Apr 2016

The aminoindanol core as a key scaffold in bifunctional organocatalysts

  • Isaac G. Sonsona,
  • Eugenia Marqués-López and
  • Raquel P. Herrera

Beilstein J. Org. Chem. 2016, 12, 505–523, doi:10.3762/bjoc.12.50

Graphical Abstract
  • ; bifunctional; organocatalysis; hydrogen bonding; Introduction The structural and chemical properties of the 1,2-aminoindanol scaffold 1 have transformed aminoindanol derivatives into versatile building blocks for the construction of catalysts and the efficient induction of chirality in asymmetric processes
  • trifluoroethylamine moiety [3][4][5]. However, it is in the field of asymmetric organocatalysis [6][7][8] where the aminoindanol core has gained more importance, being a recurrent structural motif in several organocatalytic species. Some examples are (a) the enantioselective reduction of ketones through the in situ
  • the high catalytic potential that this versatile motif exhibits [14]. The concept of bifunctionality has been extensively explored in organocatalysis in the last decade [15][16]. The bifunctional organocatalyst contains two chemical groups that interact simultaneously with the substrates. This mode of
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Published 14 Mar 2016

(Thio)urea-mediated synthesis of functionalized six-membered rings with multiple chiral centers

  • Giorgos Koutoulogenis,
  • Nikolaos Kaplaneris and
  • Christoforos G. Kokotos

Beilstein J. Org. Chem. 2016, 12, 462–495, doi:10.3762/bjoc.12.48

Graphical Abstract
  • Giorgos Koutoulogenis Nikolaos Kaplaneris Christoforos G. Kokotos Department of Chemistry, National and Kapodestrian University of Athens, Panepistimiopolis 15771, Athens, Greece 10.3762/bjoc.12.48 Abstract Organocatalysis, now running its second decade of life, is being considered one of the
  • chiral centers; organocatalysis; six-membered ring; thiourea; urea; Introduction During the last 15 years, organocatalysis has flourished and has been established as one of the three major pillars of asymmetric synthesis [1][2][3]. Among the modes of activation of organic molecules that have been
  • )ureas have been synthesized in order to utilize both hydrogen bonding interactions and enamine formation. In the last 10 years the field has witnessed the development of some new activation modes, such as SOMO catalysis [8] and photoredox organocatalysis [9]. Six-membered rings are found in many natural
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Published 10 Mar 2016

Recent advances in N-heterocyclic carbene (NHC)-catalysed benzoin reactions

  • Rajeev S. Menon,
  • Akkattu T. Biju and
  • Vijay Nair

Beilstein J. Org. Chem. 2016, 12, 444–461, doi:10.3762/bjoc.12.47

Graphical Abstract
  • ; benzoin reaction; N-heterocyclic carbenes; organocatalysis; umpolung; Introduction The benzoin reaction (or condensation) is named after the product it furnishes via a catalytic assembly of two molecules of aromatic aldehydes. One molecule of the aldehyde functions as an acyl anion and the other as a
  • that the cyanide anion can catalyze the union of two molecules of aromatic aldehydes to afford α-hydroxy ketones [1]. More than a century later, a thiazolium salt-catalysed benzoin reaction was reported by Ukai [2]. This may be regarded as an early example of organocatalysis using an azolium salt
  • reaction remained elusive due to a variety of reasons, the toxicity of cyanide catalysts being one of them. Breslow’s discovery in 1958 of the thiazolylidene-catalysed benzoin condensation via polarity reversal of aldehydes formed the conceptual basis for the later development of NHC-organocatalysis. The
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Published 09 Mar 2016

Cupreines and cupreidines: an established class of bifunctional cinchona organocatalysts

  • Laura A. Bryant,
  • Rossana Fanelli and
  • Alexander J. A. Cobb

Beilstein J. Org. Chem. 2016, 12, 429–443, doi:10.3762/bjoc.12.46

Graphical Abstract
  • asymmetric organocatalysis. This fascinating class of bifunctional catalyst offers a genuine alternative to the more commonly used thiourea systems and because of the different spacing between the functional groups, can control enantioselectivity where other organocatalysts have failed. In the main, this
  • . Keywords: bifunctional; cupreidine; cinchona; cupreine; organocatalysis; Introduction The cinchona alkaloids, comprising quinine (QN), quinidine (QD), cinchonidine (CD), cinchonine (CN, Figure 1), and their derivatives have revolutionized asymmetric catalysis owing to their privileged structures. The
  • their derivatives in asymmetric organocatalysis over the last five years or so [13][14]. The review is organized by reaction type, beginning with the Morita–Baylis–Hillman process – one of the first reactions to utilize 6’-OH-cinchona alkaloid derivatives in asymmetric organocatalysis. The focus will
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Published 07 Mar 2016

Organocatalytic asymmetric Henry reaction of 1H-pyrrole-2,3-diones with bifunctional amine-thiourea catalysts bearing multiple hydrogen-bond donors

  • Ming-Liang Zhang,
  • Deng-Feng Yue,
  • Zhen-Hua Wang,
  • Yuan Luo,
  • Xiao-Ying Xu,
  • Xiao-Mei Zhang and
  • Wei-Cheng Yuan

Beilstein J. Org. Chem. 2016, 12, 295–300, doi:10.3762/bjoc.12.31

Graphical Abstract
  • -pyrrol-2(3H)-ones bearing quaternary stereocenters were obtained in acceptable yield (up to 75%) and enantioselectivity (up to 73% ee). Keywords: asymmetric catalysis; bifunctional catalysts; Henry reaction; organocatalysis; 1H-pyrrole-2,3-diones; Introduction Asymmetric organocatalysis has been
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Published 16 Feb 2016

Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen

  • Hans Sterckx,
  • Johan De Houwer,
  • Carl Mensch,
  • Wouter Herrebout,
  • Kourosch Abbaspour Tehrani and
  • Bert U. W. Maes

Beilstein J. Org. Chem. 2016, 12, 144–153, doi:10.3762/bjoc.12.16

Graphical Abstract
  • organocatalysis in combination with molecular oxygen has received a great deal of attention from the scientific community [4][5][6][7]. Molecular oxygen is considered to be the greenest oxidant available and it is already widely employed by the commodity chemical industry [8]. However, when looking at the
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Published 27 Jan 2016

Direct estimate of the internal π-donation to the carbene centre within N-heterocyclic carbenes and related molecules

  • Diego M. Andrada,
  • Nicole Holzmann,
  • Thomas Hamadi and
  • Gernot Frenking

Beilstein J. Org. Chem. 2015, 11, 2727–2736, doi:10.3762/bjoc.11.294

Graphical Abstract
  • last two decades, these versatile compounds have been widely employed in transition metal [9][10][11][12][13] and organocatalysis [14][15][16], organometallic [17][18][19] and main group synthesis [20][21][22][23][24][25][26], and activation of small molecules [27][28]. NHCs possess a divalent C(II
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Published 24 Dec 2015

Organocatalytic and enantioselective Michael reaction between α-nitroesters and nitroalkenes. Syn/anti-selectivity control using catalysts with the same absolute backbone chirality

  • Jose I. Martínez,
  • Uxue Uria,
  • Maria Muñiz,
  • Efraím Reyes,
  • Luisa Carrillo and
  • Jose L. Vicario

Beilstein J. Org. Chem. 2015, 11, 2577–2583, doi:10.3762/bjoc.11.277

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  • all cases. Keywords: asymmetric diastereodivergent; enantioselective; Michael addition; nitroalkenes; nitroesters; organocatalysis; squaramides; Introduction The absolute stereochemistry of a molecule has a paramount influence on the properties that this compound will have when interacting with
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Published 14 Dec 2015

Convenient preparation of high molecular weight poly(dimethylsiloxane) using thermally latent NHC-catalysis: a structure-activity correlation

  • Stefan Naumann,
  • Johannes Klein,
  • Dongren Wang and
  • Michael R. Buchmeiser

Beilstein J. Org. Chem. 2015, 11, 2261–2266, doi:10.3762/bjoc.11.246

Graphical Abstract
  • , 1.6 < ÐM < 2.5) in yields >95%, using low catalyst loadings (0.2–0.1 mol %). Furthermore, the results suggest that a nucleophilic, zwitterionic mechanism is in operation, in preference to purely anionic polymerization. Keywords: latency; N-heterocyclic carbenes; ring-opening organocatalysis
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Published 20 Nov 2015

A facile synthetic route to benzimidazolium salts bearing bulky aromatic N-substituents

  • Gabriele Grieco,
  • Olivier Blacque and
  • Heinz Berke

Beilstein J. Org. Chem. 2015, 11, 1656–1666, doi:10.3762/bjoc.11.182

Graphical Abstract
  • tunable, strongly binding ligand units in complexes in the search for new materials [1][2][3][4][5] and for catalysts of homogeneous catalysis [6][7][8][9][10]. Besides that NHCs have great potential in organocatalysis [11][12][13][14][15], their electronic properties, σ-donor ability and π-back donation
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Published 17 Sep 2015

Synthesis of γ-hydroxypropyl P-chirogenic (±)-phosphorus oxide derivatives by regioselective ring-opening of oxaphospholane 2-oxide precursors

  • Iris Binyamin,
  • Shoval Meidan-Shani and
  • Nissan Ashkenazi

Beilstein J. Org. Chem. 2015, 11, 1332–1339, doi:10.3762/bjoc.11.143

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  • once binded to metals which favor a six-membered ring geometry. Moreover, these compounds could be advantageously used in organocatalysis and are commonly embedded in inorganic or organic matrix for various heterogeneous applications. Chemical structures of 2-methoxy-1,3,2-dioxaphospholane 2-oxide (1
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Published 30 Jul 2015
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