Relevant bibliographies by topics / Chiral organocatalyst

Academic literature on the topic 'Chiral organocatalyst'

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Published: 4 June 2021
Last updated: 1 February 2022

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Journal articles on the topic "Chiral organocatalyst"

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Félix, Ana Rita G., Pedro R. D. Simões, Francisco J. P. M. Sousa, M. Elisa Silva Serra, and Dina Murtinho. "Chiral Thiazolidine based Organocatalysts: Synthesis and Application in Asymmetric Aldol Reactions." Letters in Organic Chemistry 17, no. 5 (April 28, 2020): 372–80. http://dx.doi.org/10.2174/2210681209666190807155816.

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Several novel chiral organocatalysts derived from thiazolidines containing amide and thioureia functionalities were synthesized in good yields. These organocatalysts were tested in the asymmetric aldol reaction of acetone with p-nitrobenzaldehyde. Reaction parameters such as reaction time, catalyst loading and solvent were optimized. Products with conversions up to 84% and enantiomeric ratios (er) up to 84.5:15.5 (R:S) were obtained. The effect of several chiral and non-chiral additives on the reactivity and selectivity of the reaction was also evaluated. The reaction was extended to other aromatic aldehydes with the best organocatalyst and when p-bromobenzaldehyde was used, an er of 94.5:5.5 (R:S) was obtained.
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Çetin, Adnan, Ishak Bildirici, and Selçuk Gümüş. "Novel Pyrazole Derivatives Having Mono/Di Chiral Centered Group as Organocatalyst for Henry Reaction." Macedonian Journal of Chemistry and Chemical Engineering 39, no. 1 (June 9, 2020): 17. http://dx.doi.org/10.20450/mjcce.2020.1954.

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The chiral substituted pyrazole-3-carboxamides (4a-c), pyrazole-3-carboxylates (5a-c), pyrazole-3-thioureides (7a-c) and pyrazole-3,4-dicarboxamides (10a-c) were prepared via the pyrazolo-3-chlorocarbonyl 2, pyrazolo-3,4-dicarboxy methyl ester 3 with pyrazole-3-isothiocyanate 6 with different (R)-chiral amino alcohols. All of the synthesized chiral compounds binding a pyrazole skeleton were investigated as organocatalysts for asymmetric aldol reactions between nitromethane and p-nitrobenzaldehyde in the presence of CuCl. Enantiomeric excesses and the reaction yields were found to be appropriate values. Furthermore, the best organocatalyst applied in this study was identified after careful optimization of conditions. Lastly, all of the novel compounds were subjected to computational analysis at the B3LYP/6-31++G(d,p) level of theory to obtain information about their structural and electronic properties.
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Porcar, Raúl, Eduardo García-Verdugo, Belén Altava, Maria Isabel Burguete, and Santiago V. Luis. "Chiral Imidazolium Prolinate Salts as Efficient Synzymatic Organocatalysts for the Asymmetric Aldol Reaction." Molecules 26, no. 14 (July 9, 2021): 4190. http://dx.doi.org/10.3390/molecules26144190.

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Chiral imidazolium l-prolinate salts, providing a complex network of supramolecular interaction in a chiral environment, have been studied as synzymatic catalytic systems. They are demonstrated to be green and efficient chiral organocatalysts for direct asymmetric aldol reactions at room temperature. The corresponding aldol products were obtained with moderate to good enantioselectivities. The influence of the presence of chirality in both the imidazolium cation and the prolinate anion on the transfer of chirality from the organocatalyst to the aldol product has been studied. Moreover, interesting match/mismatch situations have been observed regarding configuration of chirality of the two components through the analysis of results for organocatalysts derived from both enantiomers of prolinate (R/S) and the trans/cis isomers for the chiral fragment of the cation. This is associated with differences in the corresponding reaction rates but also to the different tendencies for the formation of aggregates, as evidenced by nonlinear effects studies (NLE). Excellent activities, selectivities, and enantioselectivities could be achieved by an appropriate selection of the structural elements at the cation and anion.
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Nájera, Carmen, José Miguel Sansano, and Enrique Gómez-Bengoa. "Heterocycle-based bifunctional organocatalysts in asymmetric synthesis." Pure and Applied Chemistry 88, no. 6 (June 1, 2016): 561–78. http://dx.doi.org/10.1515/pac-2016-0403.

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AbstractDifferent chiral bifunctional organocatalysts derived from trans-cyclohexane-1,2-diamine bearing different types of guanidine units able to form-hydrogen bonding activation have been designed. Conformational rigid 2-aminobenzimidazoles bearing a tertiary amino group have been used in enantioselective Michael type reactions of activated methylene compounds to nitroalkenes. The C2 symmetric bis(2-aminobenzimidazole) derivatives the appropriate organocatalyst for the conjugate addition of 1,3-dicarbonyl compounds to maleimides as well as for the SN1 reaction of benzylic alcohols with carbon nucleophiles. 2-Aminobenzimidazoles bearing a primary amino group have shown excellent catalytic activity in the Michael reaction of aldehydes to maleimides and nitroalkenes. Diastereomeric 2-aminopyrimidines bearing a prolinamide unit have been incorporated in the trans-cyclohexane-1,2-diamine scaffold and have been used for the inter- and intra-molecular direct aldol reaction under solvent-free conditions. For the Michael reaction of aldehydes with maleimides the primary amine 2-aminopyrimidine has shown excellent efficiency as organocatalyst. The bifunctional character of these organocatalysts has been demonstrated by means of DFT calculations.
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Mangawa, Shrawan K., Ashawani K. Singh, and Satish K. Awasthi. "Design and synthesis of a s-triazene based asymmetric organocatalyst and its application in enantioselective alkylation." RSC Advances 5, no. 75 (2015): 61144–47. http://dx.doi.org/10.1039/c5ra11209e.

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Vural, Ummu, Mustafa Durmaz, and Abdulkadir Sirit. "A novel calix[4]arene-based bifunctional squaramide organocatalyst for enantioselective Michael addition of acetylacetone to nitroolefins." Organic Chemistry Frontiers 3, no. 6 (2016): 730–36. http://dx.doi.org/10.1039/c6qo00135a.

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A new chiral calix[4]arene-based organocatalyst 3 bearing bis-squaramide moieties was designed and synthesized from p-tert-butylcalix[4]arene. This bifunctional organocatalyst was used in the enantioselective conjugate addition of acetyl acetone to β-nitrostyrenes. The corresponding adducts were obtained in good to excellent yields with high enantioselectivities.
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Wagner, Christian, Andreas F. Kotthaus, and Stefan F. Kirsch. "The asymmetric reduction of imidazolinones with trichlorosilane." Chemical Communications 53, no. 32 (2017): 4513–16. http://dx.doi.org/10.1039/c7cc01561e.

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Geng, Zhi-Cong, Jian Chen, Ning Li, Xiao-Fei Huang, Yong Zhang, Ya-Wen Zhang, and Xing-Wang Wang. "Organocatalytic cascade aza-Michael/hemiacetal reaction between disubstituted hydrazines and α,β-unsaturated aldehydes: Highly diastereo- and enantioselective synthesis of pyrazolidine derivatives." Beilstein Journal of Organic Chemistry 8 (October 9, 2012): 1710–20. http://dx.doi.org/10.3762/bjoc.8.195.

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The catalytic synthesis of nitrogen-containing heterocycles is of great importance to medicinal and synthetic chemists, and also a challenge for modern chemical methodology. In this paper, we report the synthesis of pyrazolidine derivatives through a domino aza-Michael/hemiacetal sequence with chiral or achiral secondary amines as organocatalysts. Thus, a series of achiral pyrazolidine derivatives were obtained with good yields (up to 90%) and high diastereoselectivities (>20:1) with pyrrolidine as an organocatalyst, and enantioenriched pyrazolidines are also achieved with good results (up to 86% yield, >10/1 regioselectivity, >20:1 dr, 99% ee) in the presence of (S)-diphenylprolinol trimethylsilyl ether catalyst.
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Zhou, Muxing, Ende He, Lu Zhang, Jianzhong Chen, Zhenfeng Zhang, Yangang Liu, and Wanbin Zhang. "Development of a new bicyclic imidazole nucleophilic organocatalyst for direct enantioselective C-acylation." Organic Chemistry Frontiers 6, no. 24 (2019): 3969–72. http://dx.doi.org/10.1039/c9qo01025d.

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Haraguchi, Naoki, and Shinichi Itsuno. "ChemInform Abstract: Polymer-Immobilized Chiral Organocatalyst." ChemInform 43, no. 17 (March 29, 2012): no. http://dx.doi.org/10.1002/chin.201217232.

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Dissertations / Theses on the topic "Chiral organocatalyst"

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Ortayli, Oytun. "Asymmetric Synthesis Of 1,4-diamine Based Chiral Ligand And Organocatalyst And Their Applications." Master's thesis, METU, 2010. http://etd.lib.metu.edu.tr/upload/12612335/index.pdf.

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Novel 1,4-chiral diamine ligand possessing a trans-9,10-dihydro-9,10-ethanoanthracene backbone was synthesized. The synthetic plan involves first LiAlH4 reduction of the Diels-Alder adduct obtained by reaction of dimenthyl fumarate and anthracene, which is followed by reacting the corresponding alcohol and subsequent attachment of mesylate and triflate units to get good leaving groups which are available substances for introducing nitrogen units via SN2 type reactions. Consequently, by using dimesyl ester and ditriflate esters five catalysts 27, 29, 30, 33 and 38 were synthesized. The first four catalysts 27, 29, 30 and 33 were used in transfer hydrogenation reactions with transition metal whereas catalyst 38 used as an organocatalyst in direct aldol reaction between acetone and p-nitrobenzaldehyde.
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Joyce, Jesse Jo. "The Development and Use of Chiral 4-Dimethylaminopyridine-N-Oxide as an Organocatalyst." Thesis, North Dakota State University, 2018. https://hdl.handle.net/10365/29269.

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Document incorrectly classified as a dissertation on title page (decision to classify as a thesis from NDSU Graduate School)
Organocatalysis is a field that has bloomed over the last decades. With the field’s promise of being able to mimic nature and afford products in a synergistic manner to traditional Lewis acid catalysis, several interesting discoveries have been made. Owing to the vastness of the field as it exists today, this document will focus on two main aspects; cinchona alkaloid (and derivatives) as used in common carbon-carbon bond forming reactions and kinetic resolution via 4-dimethyl aminopyridine-N-oxide derivative driven acylation. Kinetic resolution via organocatalysis has the potential to react one enantiomer of a racemic mixture without affecting the other. The highlight of this screening was an s factor of 9 which was produced using optimized conditions using a catalyst designated DMAPO-IV. There remains much to do in improving the system and elucidating the scope of this catalytic system this report details the efforts made thus far.
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Kucukdisli, Murat. "Asymmetric Synthesis Of Chiral Camphor Fused Pyridine Type Novel Organocatalysts." Master's thesis, METU, 2009. http://etd.lib.metu.edu.tr/upload/12610790/index.pdf.

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Chiral pyridines as organocatalysts have been used in asymmetric organic synthesis in recent years. The asymmetric synthesis of camphor fused pyridine type novel organocatalysts were perfomed starting from cheap and easily available natural (+)-camphor. Using camphor fused pyridine skeleton, six organocatalysts 29, 32, 33, 38, 40, and 41were successfully synthesized. The first four nucleophilic and Lewis base catalysts 29, 32, and 33 are different P-oxides and P,N-dioxides which were tested in allylation of aldehydes via allyltrichlorosilane. L-proline amide 38 and D-proline amide 40 can be named as secondary amine catalyst. They were tested in direct aldol reaction between acetone and aromatic aldehydes in aqueous medium. Final group of catalyst is hydrogen bonding type catalyst which is thiourea based 41.
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Lamprianidis, Panagiotis. "Photoredox catalysis with 10-phenyl-10H- phenothiazine and synthesis of a photocatalytic chiral proline-based organocatalyst." Thesis, KTH, Organisk kemi, 2020. http://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-293510.

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Photoredox catalysis applications for the purpose of new synthetic routes in organic and sustainable chemistry are hot topics in organic synthesis today. In the present study, the synthesis of a chiral proline-based organocatalyst functionalized with 10-phenyl-10H phenothiazine (PTH) photocatalytic moietiesis investigated and attempted for the first time. PTH, an organic photocatalyst, isstudied for its photocatalytic activity in different organic reactions, such as dehalogenation of aromatic halides and the pinacol coupling reaction between aromatic aldehydes. These transformations are otherwise difficult to achieve without a suitable catalyst and the reactions were performed with moderate to high yields.
Applikationer av photoredox-katalys med syftet att generera nya syntetiska vägar inom organisk och hållbar kemi är populära ämnen i organisk syntes idag. I denna studien undersöktes för första gången syntesen av en kiral prolinbaserad organokatalysator som är funktionaliserad med fotokatalytiska enheter (10-fenyl-10H-fenotiazin (PTH)). Den fotokatalytiska aktiviteten av PTH studerades för olika organiska reaktioner, såsom t.ex. dehalogenering av aromatiska halider och pinacolkopplingar mellan aromatiska aldehyder. Dessa transformationer är annars svåra att uppnå utan en lämplig fotokatalysator och reaktionerna utfördes med måttliga till höga utbyten.
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Jackson, Daniel Paul. "Synthesis, Characterization, and Applications of Chiral Amino Acid Derived Pyrrolines." University of Akron / OhioLINK, 2015. http://rave.ohiolink.edu/etdc/view?acc_num=akron1430819653.

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Matsumoto, Akira. "Studies on Organocatalytic Asymmetric Construction of Chiral Carbinols." Kyoto University, 2019. http://hdl.handle.net/2433/242517.

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Curati, Federico. "Synthesis of a chiral, water soluble porphyrin containing a pyrrolidine unit and initial study of its catalytic activity." Master's thesis, Alma Mater Studiorum - Università di Bologna, 2018. http://amslaurea.unibo.it/16731/.

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Asymmetric organocatalysis have taken hold in the last decades due to affordability and lack of toxicity of their catalysts. Unfortunately, organocatalytic enantioselective reactions in an environmentally friendly and safe solvent as water are still scarce. During the training internship our aim has been to find an effective water soluble organocatalyst able to drive in an enantioselective fashion a reaction, to maximize the diasteromeric and the enantiomeric excess. Pursuing this objective we synthesized a meso 3-sulfonatophenyl porphyrin with a chiral aminoaldehyde substituent, with the sulfonate-groups allowing its solubilization in water and the chiral group which should improve the enantioselectivity. The chiral aldehyde has been prepared starting from L-proline, a widely used organocatalyst, and finally tried in an aldol reaction, giving excellent yield, moderate diastereoselectivity and very low enantiomeric excess. The reaction products can be easily removed washing in organic solvent and the catalyst can be recovered by aggregation in acidic medium.
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Nakatsu, Hiroki. "Studies on Chiral Bronsted Acid-Catalyzed Activation of Imino Functionalities." 京都大学 (Kyoto University), 2014. http://hdl.handle.net/2433/188505.

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Sugimoto, Hisashi. "Studies on Control of Stereo- and Regioselectivity in Conjugate Additions of Aldehydes Catalyzed by Axially Chiral Biaryl-Based Amines." 京都大学 (Kyoto University), 2015. http://hdl.handle.net/2433/199123.

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Beck, Daniel Antony Speedie, and beckautomatic@gmail com. "Stereoselective intramolecular Michael addition reactions of pyrrole and their application to natural product syntheses." The Australian National University. Research School of Chemistry, 2006. http://thesis.anu.edu.au./public/adt-ANU20070130.130009.

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Chapter one; “(-)-Rhazinilam and (-)-Rhazinal: Alkaloids with Anti-mitotic Properties Derived from Kopsia teoi”, provides the background information behind the motives that initiated this research project. The plant alkaloid (-)-rhazinilam [(-)-1] and its naturally-occurring derivative (-)-rhazinal [(-)-13] both exhibit potent anti-mitotic activities and, as such, are interesting targets for total synthesis. Chapter one is a review of the literature regarding these two compounds and discusses the occurrence, proposed biosynthetic origins, structural elucidation and biological activites of compound (-)-1 and that of its analogues including alkaloid (-)-13. Previous total syntheses of these two compounds are then examined, concluding with the only reported total synthesis of compound (-)-13. Developed within the Banwell research group, this total synthesis produced the racemic modification of alkaloid (-)-13 due to a lack of any stereocontrol in the key intramolecular Michael addition step. This unprecedented key step, involving cyclisation of the C2 of pyrrole onto an N-tethered and ?,?-disubstituted acrylate to produce a quaternary-carbon stereogenic centre, would be of greatly enhanced utility if it could be achieved in a catalytic-enantioselective fashion. The realisation of this goal is the central aim of the research conducted within this thesis. ¶ Chapter two; “Investigating Asymmetric Induction in the Intramolecular Michael Addition of pyrrole to N-Tethered Acrylates and Related Species”, introduces the model study used to direct research towards achieving the goal of asymmetric induction in the title process. The model is a somewhat simplified version of the original process used in the total synthesis of compound (-)-13 involving cyclisation of the C2 of pyrrole onto an N-tethered and ?-monosubstituted Michael acceptor, to produce a tertiary-carbon stereogenic centre. This simplification allows the rapid synthesis of a broad range of potential substrates for use in the title process, thus enabling the investigation of various different approaches to inducing asymmetry therein. High levels of asymmetric induction are observed with the use of chiral substrates or catalysts, facilitating the synthesis of both 6- and 7-membered rings annulated to pyrrole with construction of the relevant tertiary-carbon stereogenic centre in enantio-enriched form. For the reactions producing a 6-membered ring annulated to pyrrole, unambiguous proof of the absolute sense of asymmetric induction observed in the intramolecular Michael addition event is established using a chemical correlation study involving elaboration of a key indolizine-type cyclisation product, to the plant alkaloid of known absolute stereochemistry, (-)-tashiromine [(-)-75]. For the reaction producing a 7-membered ring annulated to pyrrole, the same information is obtained via X-ray crystallographic analyses of a dibrominated derivative of a key pyrroloazepine-type cyclisation product. ¶ Chapter three “An Enantioselective Total Synthesis of the Alkaloid (-)-Rhazinal: An Anti-mitotic Agent Isolated from Kopsia teoi.”, focuses on the application of methodology developed in the previous chapter, to the original goal of inducing asymmetry in the intramolecular Michael addition reaction, involving cyclisation of the C2 of pyrrole onto an N-tethered and ?,?-disubstituted acrylate to produce a quaternary-carbon stereogenic centre. This is ultimately achieved in a catalytic-enantioselective fashion, resulting in the first such total synthesis of the anti-mitotic alkaloid (-)-rhazinal [(-)-13]. ¶ Chapter four “Extending the Reaction Manifold to the Syntheses of Related Natural Products: A Formal Total Synthesis of (+)-Aspidospermidine and Syntheses of (-)-Rhazinilam and (-)-Leuconolam from (-)-Rhazinal”, describes three extensions to the reaction manifold used in the enantioselective total synthesis of alkaloid (-)-13: The acquisition in an enantioselective manner, of an intermediate previously obtained in racemic form, en route to the racemic modification of the natural product (±)-aspidospermidine [(±)-134], constitutes a formal and enantioselective total synthesis of (+)-aspidospermidine [(+)-134]. The direct deformylation of (-)-rhazinal [(-)-13], is carried out, to produce the parent alkaloid (-)-rhazinilam [(-)-1]. The pyrrole ring present in (-)-rhazinilam [(-)-1] is oxidised, to produce the related natural product (-)-Leuconolam [(-)-12] which has not, hitherto, been prepared by total synthesis. ¶Chapter five contains the experimental procedures and characterisation data associated with compounds described in chapters two to four.
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Book chapters on the topic "Chiral organocatalyst"

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Haraguchi, Naoki, and Shinichi Itsuno. "Polymer-Immobilized Chiral Organocatalyst." In Polymeric Chiral Catalyst Design and Chiral Polymer Synthesis, 17–61. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2011. http://dx.doi.org/10.1002/9781118063965.ch2.

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Uraguchi, Daisuke, Kohsuke Ohmatsu, and Takashi Ooi. "Chiral C2Catalysts." In Comprehensive Enantioselective Organocatalysis, 161–93. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2013. http://dx.doi.org/10.1002/9783527658862.ch7.

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David, Olivier R. P. "Planar Chiral Catalysts." In Comprehensive Enantioselective Organocatalysis, 195–219. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2013. http://dx.doi.org/10.1002/9783527658862.ch8.

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Mahrwald, Rainer. "Chiral Imidazolidinone (MacMillan's) Catalyst." In Comprehensive Enantioselective Organocatalysis, 69–95. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2013. http://dx.doi.org/10.1002/9783527658862.ch4.

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Jakab, Gergely, and Peter R. Schreiner. "Brønsted Acids: Chiral (Thio)urea Derivatives." In Comprehensive Enantioselective Organocatalysis, 315–41. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2013. http://dx.doi.org/10.1002/9783527658862.ch12.

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Shirakawa, Seiji, and Keiji Maruoka. "Chiral Onium Salts (Phase-Transfer Reactions)." In Comprehensive Enantioselective Organocatalysis, 365–79. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2013. http://dx.doi.org/10.1002/9783527658862.ch14.

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Breitenlechner, S., P. Selig, and T. Bach. "Chiral Organocatalysts for Enantioselective Photochemical Reactions." In Ernst Schering Foundation Symposium Proceedings, 1–50. Berlin, Heidelberg: Springer Berlin Heidelberg, 2007. http://dx.doi.org/10.1007/2789_2007_065.

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Kampen, Daniela, Corinna M. Reisinger, and Benjamin List. "Chiral Brønsted Acids for Asymmetric Organocatalysis." In Topics in Current Chemistry, 395–456. Berlin, Heidelberg: Springer Berlin Heidelberg, 2009. http://dx.doi.org/10.1007/128_2009_1.

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Kampen, Daniela, Corinna M. Reisinger, and Benjamin List. "Chiral Brønsted Acids for Asymmetric Organocatalysis." In Topics in Current Chemistry, 1–37. Berlin, Heidelberg: Springer Berlin Heidelberg, 2009. http://dx.doi.org/10.1007/978-3-642-02815-1_1.

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Kee, Choon Wee, and Choon-Hong Tan. "Chapter 23. Chiral Guanidines as Asymmetric Organocatalysts." In Green Chemistry Series, 381–405. Cambridge: Royal Society of Chemistry, 2015. http://dx.doi.org/10.1039/9781782626435-00381.

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Conference papers on the topic "Chiral organocatalyst"

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Vo-Thanh, Giang, and Huong Nguyen Thi Thu. "Synthesis of Chiral Thiourea-Phosphine Organocatalysts derived from L-Proline." In The 19th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2015. http://dx.doi.org/10.3390/ecsoc-19-a058.

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