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Journal articles on the topic 'Prolinamid'

Author: Grafiati
Published: 24 April 2022
Last updated: 30 July 2025

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1

Maciá, María, Raúl Porcar, Vicente Martí-Centelles, Eduardo García-Verdugo, Maria Isabel Burguete, and Santiago V. Luis. "Rational Design of Simple Organocatalysts for the HSiCl3 Enantioselective Reduction of (E)-N-(1-Phenylethylidene)aniline." Molecules 26, no. 22 (2021): 6963. http://dx.doi.org/10.3390/molecules26226963.

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Prolinamides are well-known organocatalysts for the HSiCl3 reduction of imines; however, custom design of catalysts is based on trial-and-error experiments. In this work, we have used a combination of computational calculations and experimental work, including kinetic analyses, to properly understand this process and to design optimized catalysts for the benchmark (E)-N-(1-phenylethylidene)aniline. The best results have been obtained with the amide derived from 4-methoxyaniline and the N-pivaloyl protected proline, for which the catalyzed process is almost 600 times faster than the uncatalyzed
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2

Hoffm�ller, Winfried, Kurt Polborn, J�rg Knizek, Heinrich N�th, and Wolfgang Beck. "Metallkomplexe mit biologisch wichtigen Liganden. XCV. ?5- Pentamethylcyclopentadienyl-Rhodium-, -Iridium-, (?6-Benzol)-Ruthenium- und Phosphan-Palladium-Komplexe von Prolinmethylester und Prolinamid." Zeitschrift f�r anorganische und allgemeine Chemie 623, no. 12 (1997): 1903–11. http://dx.doi.org/10.1002/zaac.19976231214.

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3

Sundararaju, Kavya, Ramesh Kumar Chidambaram, and Radhakrishnan Narayanaswamy. "SYNTHESIS, CHARACTERIZATION, AND MOLECULAR DOCKING ANALYSIS OF PROLINE (PYRROLIDINE 2-CARBOXYLIC ACID) AND PROLINAMIDE (PYRROLIDINE 2-CARBOXYLIC ACID AMIDE) ISOMERS AS BACTERIAL COLLAGENASE INHIBITORS." Asian Journal of Pharmaceutical and Clinical Research 12, no. 1 (2019): 487. http://dx.doi.org/10.22159/ajpcr.2018.v12i1.29894.

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Objectives: D-proline is an isomer of L-proline, naturally occurring amino acid. Apart from this, several proline homologs and analogs are available in nature. For instance, hydroxyproline one of proline analog plays a key role in collagen function. Inhibition of collagenase activity plays a significant role in protecting the unbalanced turnover of collagen, caused due to inflammation and photoaging of skin. This prompted us to carry out the study on proline and prolinamide isomers.Methods: These proline and prolinamide isomers were evaluated on the docking behavior of bacterial collagenase us
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4

Sundararaju, Kavya, Ramesh Kumar Chidambaram, and Radhakrishnan Narayanaswamy. "SYNTHESIS, CHARACTERIZATION, AND MOLECULAR DOCKING ANALYSIS OF PROLINE (PYRROLIDINE 2-CARBOXYLIC ACID) AND PROLINAMIDE (PYRROLIDINE 2-CARBOXYLIC ACID AMIDE) ISOMERS AS BACTERIAL COLLAGENASE INHIBITORS." Asian Journal of Pharmaceutical and Clinical Research 12, no. 1 (2019): 487. http://dx.doi.org/10.22159/ajpcr.2019.v12i1.29894.

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Objectives: D-proline is an isomer of L-proline, naturally occurring amino acid. Apart from this, several proline homologs and analogs are available in nature. For instance, hydroxyproline one of proline analog plays a key role in collagen function. Inhibition of collagenase activity plays a significant role in protecting the unbalanced turnover of collagen, caused due to inflammation and photoaging of skin. This prompted us to carry out the study on proline and prolinamide isomers.Methods: These proline and prolinamide isomers were evaluated on the docking behavior of bacterial collagenase us
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5

Du, Ganhong, Jun Ling, Fangyu Hu, Keyuan Liu, Long Ye, and Liming Jiang. "Bioinspired Polymer-Bound Organocatalysts for Direct Asymmetric Aldol Reaction: Experimental and Computational Studies." Catalysts 9, no. 5 (2019): 398. http://dx.doi.org/10.3390/catal9050398.

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A series of poly(2-oxazoline) (POX) derivatives bearing prolinamide pendants were designed as organocatalysts and evaluated in the direct asymmetric aldol reaction between aromatic aldehydes and cyclic ketones. The structural variation of the alkyl spacer connecting the polymer backbone with the catalytic unit was applied so as to deduce structure–performance relationships combined with comparable experiments from model catalysts. Results showed that the POX-bound prolinamides can promote the aldol reaction more effectively as compared to their small-molecular and non-POX-bound analogs. The ca
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6

Mousa, Mai H. A., Nermin S. Ahmed, Kai Schwedtmann, et al. "Design and Synthesis of Novel Symmetric Fluorene-2,7-Diamine Derivatives as Potent Hepatitis C Virus Inhibitors." Pharmaceuticals 14, no. 4 (2021): 292. http://dx.doi.org/10.3390/ph14040292.

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Hepatitis C virus (HCV) is an international challenge. Since the discovery of NS5A direct-acting antivirals, researchers turned their attention to pursue novel NS5A inhibitors with optimized design and structure. Herein we explore highly potent hepatitis C virus (HCV) NS5A inhibitors; the novel analogs share a common symmetrical prolinamide 2,7-diaminofluorene scaffold. Modification of the 2,7-diaminofluorene backbone included the use of (S)-prolinamide or its isostere (S,R)-piperidine-3-caboxamide, both bearing different amino acid residues with terminal carbamate groups. Compound 26 exhibite
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7

Arivalagan, Premkumar Rathinam, and Yan Zhao. "Interfacial catalysis of aldol reactions by prolinamide surfactants in reverse micelles." Organic & Biomolecular Chemistry 13, no. 3 (2015): 770–75. http://dx.doi.org/10.1039/c4ob02074j.

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8

Yadav, Geeta Devi, and Surendra Singh. "(l)-Prolinamide imidazolium hexafluorophosphate ionic liquid as an efficient reusable organocatalyst for direct asymmetric aldol reaction in solvent-free condition." RSC Advances 6, no. 102 (2016): 100459–66. http://dx.doi.org/10.1039/c6ra23652a.

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9

Chauhan, Ajay, Sushovan Paladhi, Manish Debnath, and Jyotirmayee Dash. "Selective recognition of c-MYC G-quadruplex DNA using prolinamide derivatives." Organic & Biomolecular Chemistry 14, no. 24 (2016): 5761–67. http://dx.doi.org/10.1039/c6ob00177g.

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10

Kucherenko, A. S., A. A. Kostenko, V. V. Gerasimchuk, and S. G. Zlotin. "Stereospecific diaza-Cope rearrangement as an efficient tool for the synthesis of DPEDA pyridine analogs and related C2-symmetric organocatalysts." Organic & Biomolecular Chemistry 15, no. 33 (2017): 7028–33. http://dx.doi.org/10.1039/c7ob01852e.

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11

Calles, María, Julio Puigcerver, Diego A. Alonso, Mateo Alajarin, Alberto Martinez-Cuezva, and Jose Berna. "Enhancing the selectivity of prolinamide organocatalysts using the mechanical bond in [2]rotaxanes." Chemical Science 11, no. 14 (2020): 3629–35. http://dx.doi.org/10.1039/d0sc00444h.

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12

Dodda, Rajasekhar, Sampak Samanta, Matthew Su, and John Cong-Gui Zhao. "Synthesis of 1,2-Diamine Bifunctional Catalysts for the Direct Aldol Reaction Through Probing the Remote Amide Hydrogen." Current Organocatalysis 6, no. 2 (2019): 171–76. http://dx.doi.org/10.2174/2213337206666190301155247.

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Background: While proline can catalyze the asymmetric direct aldol reactions, its catalytic activity and catalyst turnover are both low. To improve the catalytic efficiency, many prolinebased organocatalysts have been developed. In this regard, prolinamide-based bifunctional catalysts have been demonstrated by us and others to be highly efficient catalysts for the direct aldol reactions. Results: Using the β-acetamido- and β-tosylamidoprolinamide catalysts, the highly enantio- and diastereoselective direct aldol reactions between enolizable ketones and aldehydes were achieved (up to >99% ee
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13

Prasanth, Thumpati, Gargi Chakraborti, Tirtha Mandal, Velayutham Ravichandiran, and Jyotirmayee Dash. "Cycloaddition of N-sulfonyl and N-sulfamoyl azides with alkynes in aqueous media for the selective synthesis of 1,2,3-triazoles." Green Chemistry 24, no. 2 (2022): 911–15. http://dx.doi.org/10.1039/d1gc03340a.

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14

Zhang, Lin, Ken Yamazaki, Jamie A. Leitch, et al. "Dual catalytic enantioselective desymmetrization of allene-tethered cyclohexanones." Chemical Science 11, no. 28 (2020): 7444–50. http://dx.doi.org/10.1039/d0sc02878a.

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The construction of enantioenriched azabicyclo[3.3.1]nonan-6-one heterocycles via an enantioselective desymmetrization of allene-linked cyclohexanones, enabled through a dual prolinamide/copper(i) catalytic system, is described.
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15

Wang, Rui, Enjie Xu, Zhenming Su та ін. "Preparation of prolinamide with adamantane for aldol reaction catalysis in brine and separation using a poly(AN-MA-β-CD) nanofibrous film via host–guest interaction". RSC Advances 8, № 50 (2018): 28376–85. http://dx.doi.org/10.1039/c8ra04802a.

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Prolinamide with adamantane catalyzed the aldol reaction. The reaction of cyclohexanone with m-nitrobenzaldehyde assessed recyclability of catalyst. After run, the catalyst was adsorbed with nanofibrous of polymer via host–guest interaction.
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16

Peczkowski, Gary R., Philip G. E. Craven, Darren Stead, and Nigel S. Simpkins. "2,7-Diazabicyclo[2.2.1]heptanes: novel asymmetric access and controlled bridge-opening." Chemical Communications 55, no. 29 (2019): 4214–17. http://dx.doi.org/10.1039/c8cc10263e.

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Organocatalysed asymmetric Michael additions of substituted triketopiperazines to enones afford products in high yield and enantiomeric ratio (er). Further modification delivers products possessing natural product (NP) scaffolds including diazabicyclo[2.2.1]heptane, prolinamide and harmicine.
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17

Chakraborti, Gargi, Tirtha Mandal, Charles Patriot Roy, and Jyotirmayee Dash. "A [3+2] cycloaddition-1,2-acyl migration-hydrolysis cascade for regioselective synthesis of 1,2,3-triazoles in water." Chemical Communications 57, no. 64 (2021): 7970–73. http://dx.doi.org/10.1039/d1cc02801d.

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A [3+2] cycloaddition, 1,2-acyl migration and hydrolysis cascade is delineated for the synthesis of 2H-1,2,3-triazoles via the regioselective formation of N<sup>2</sup>-carboxyalkylated triazoles using a prolinamide ligand in water.
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18

Osinubi, Adejoke, Josephat Izunobi, Xiaoguang Bao, et al. "Synthesis and in vitro anticancer activities of substituted N -(4′-nitrophenyl)- l -prolinamides." Royal Society Open Science 7, no. 9 (2020): 200906. http://dx.doi.org/10.1098/rsos.200906.

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Prolinamides are present in secondary metabolites and have wide-ranging biological properties as well as antimicrobial and cytotoxic activities. N -(4′-substituted phenyl)- l -prolinamides 4a – 4w were synthesized in two steps, starting from the condensation of p -fluoronitrobenzene 1a – 1b with l -proline 2a – 2b , under aqueous–alcoholic basic conditions to afford N -aryl- l -prolines 3a – 3c , which underwent amidation via a two-stage, one-pot reaction involving SOCl 2 and amines, to furnish l -prolinamides in 20–80% yield. The cytotoxicities of 4a – 4w against four human carcinoma cell lin
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19

Wang, Yongchao, Dong Li, Jun Lin, and Kun Wei. "Organocatalytic asymmetric Michael addition of aldehydes and ketones to nitroalkenes catalyzed by adamantoyl l-prolinamide." RSC Advances 5, no. 8 (2015): 5863–74. http://dx.doi.org/10.1039/c4ra11214h.

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20

Yadav, Geeta Devi, Deepa, and Surendra Singh. "Prolinamide‐Catalysed Asymmetric Organic Transformations." ChemistrySelect 4, no. 19 (2019): 5591–618. http://dx.doi.org/10.1002/slct.201900764.

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21

Wang, Yao, Huifang Shen, Le Zhou, Fangyu Hu, Shoulei Xie, and Liming Jiang. "Novel poly(2-oxazoline)s with pendant l-prolinamide moieties as efficient organocatalysts for direct asymmetric aldol reaction." Catalysis Science & Technology 6, no. 17 (2016): 6739–49. http://dx.doi.org/10.1039/c6cy00448b.

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22

Munegumi, Toratane, Tetsuya Maruyama, Michiaki Takasaki та Kaoru Harada. "Diastereoselective Catalytic Hydrogenation ofNα-Pyruvoyl-(S)-prolinamide". Bulletin of the Chemical Society of Japan 63, № 6 (1990): 1832–34. http://dx.doi.org/10.1246/bcsj.63.1832.

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23

Fuentes de Arriba, Ángel L., Luis Simón, César Raposo, et al. "Imidazolidinone intermediates in prolinamide-catalyzed aldol reactions." Organic & Biomolecular Chemistry 8, no. 13 (2010): 2979. http://dx.doi.org/10.1039/b926284a.

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24

Huelgas, Gabriela, Ratnasamy Somanathan, Julio M. Hernández Pérez, et al. "Homochiral bifunctional L ‐prolinamide‐ and L‐ bis‐prolinamide‐catalyzed asymmetric aldol reactions performed in wet solvent‐free conditions." Chirality 33, no. 1 (2020): 22–36. http://dx.doi.org/10.1002/chir.23283.

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25

Zhao, C. G., та R. Dodda. "l-Prolinamide-Catalyzed Enantioselective Synthesis of α-Hydroxyphosphonates". Synfacts 2006, № 12 (2006): 1282. http://dx.doi.org/10.1055/s-2006-949503.

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26

Valle, G., M. Crisma, and C. Toniolo. "Structure of N-pivaloyl-N'-methyl-L-prolinamide." Acta Crystallographica Section C Crystal Structure Communications 44, no. 5 (1988): 850–53. http://dx.doi.org/10.1107/s0108270187012526.

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27

Mohebbi, Ali, Marzieh Eskandarzadeh, Hanieh Zangi, and Marzie Fatehi. "In silico study of alkaloids with quercetin nucleus for inhibition of SARS-CoV-2 protease and receptor cell protease." PLOS ONE 19, no. 4 (2024): e0298201. http://dx.doi.org/10.1371/journal.pone.0298201.

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Covid-19 disease caused by the deadly SARS-CoV-2 virus is a serious and threatening global health issue declared by the WHO as an epidemic. Researchers are studying the design and discovery of drugs to inhibit the SARS-CoV-2 virus due to its high mortality rate. The main Covid-19 virus protease (Mpro) and human transmembrane protease, serine 2 (TMPRSS2) are attractive targets for the study of antiviral drugs against SARS-2 coronavirus. Increasing consumption of herbal medicines in the community and a serious approach to these drugs have increased the demand for effective herbal substances. Alk
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28

Puliti, R., C. A. Mattia, and T. H. Lilley. "Structure of N-acetyl-L-leucyl-L-prolinamide monohydrate." Acta Crystallographica Section C Crystal Structure Communications 48, no. 4 (1992): 709–12. http://dx.doi.org/10.1107/s0108270191011162.

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29

Fu, Yu-Qin, Zai-Chun Li, Li-Na Ding, Jing-Chao Tao, Sheng-Hong Zhang, and Ming-Sheng Tang. "Direct asymmetric aldol reaction catalyzed by simple prolinamide phenols." Tetrahedron: Asymmetry 17, no. 24 (2006): 3351–57. http://dx.doi.org/10.1016/j.tetasy.2006.12.008.

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30

Kumar, Togapur Pavan, Nemali Manjula, and Kumar Katragunta. "Asymmetric aldol reactions of isatins catalyzed by phthalimido-prolinamide." Tetrahedron: Asymmetry 26, no. 21-22 (2015): 1281–84. http://dx.doi.org/10.1016/j.tetasy.2015.09.018.

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31

Qu, Chengke, Wenshan Zhao, Lei Zhang, and Yuanchen Cui. "Preparation of Immobilized L-Prolinamide Via Enzymatic Polymerization of Phenolic L-Prolinamide and Evaluation of Its Catalytic Performance for Direct Asymmetric Aldol Reaction." Chirality 26, no. 4 (2014): 209–13. http://dx.doi.org/10.1002/chir.22302.

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32

Li, Xiaowei, and Yan Zhao. "Environmental modulation of chiral prolinamide catalysts for stereodivergent conjugate addition." Journal of Catalysis 406 (February 2022): 126–33. http://dx.doi.org/10.1016/j.jcat.2022.01.003.

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33

Sul, Soohwan, Denis Karaiskaj, Ying Jiang, and Nien-Hui Ge. "Conformations ofN-Acetyl-l-Prolinamide by Two-Dimensional Infrared Spectroscopy†." Journal of Physical Chemistry B 110, no. 40 (2006): 19891–905. http://dx.doi.org/10.1021/jp062039h.

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34

Revelou, Panagiota, Christoforos G. Kokotos, and Panagiota Moutevelis-Minakakis. "Novel prolinamide–ureas as organocatalysts for the asymmetric aldol reaction." Tetrahedron 68, no. 42 (2012): 8732–38. http://dx.doi.org/10.1016/j.tet.2012.08.023.

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35

Xiao, Jun-An, Chao-Ming Wang, Jing Wang, Guang-Chuan Ou, Xing-Yu Zhang, and Hua Yang. "Highly stereoselective synthesis of novel spiroimidazolidinones directed by pyridine prolinamide." Tetrahedron 71, no. 5 (2015): 805–12. http://dx.doi.org/10.1016/j.tet.2014.12.055.

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36

Schwab, Ricardo S., Fábio Z. Galetto, Juliano B. Azeredo, Antonio L. Braga, Diogo S. Lüdtke, and Márcio W. Paixão. "Organocatalytic asymmetric aldol reactions mediated by a cysteine-derived prolinamide." Tetrahedron Letters 49, no. 34 (2008): 5094–97. http://dx.doi.org/10.1016/j.tetlet.2008.06.031.

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37

Kumar, Togapur Pavan, Rapelli Chandra Shekhar, Kondepudi Sugnana Sunder, and Rajesh Vadaparthi. "Myrtanyl-prolinamide: a new chiral organocatalyst for stereoselective aldol reactions." Tetrahedron: Asymmetry 26, no. 10-11 (2015): 543–47. http://dx.doi.org/10.1016/j.tetasy.2015.03.009.

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38

Chimni, Swapandeep Singh, Dinesh Mahajan, and V. V. Suresh Babu. "Protonated chiral prolinamide catalyzed enantioselective direct aldol reaction in water." Tetrahedron Letters 46, no. 34 (2005): 5617–19. http://dx.doi.org/10.1016/j.tetlet.2005.06.112.

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39

Fotaras, Stamatis, Christoforos G. Kokotos, and George Kokotos. "A tripeptide-like prolinamide-thiourea as an aldol reaction catalyst." Organic & Biomolecular Chemistry 10, no. 29 (2012): 5613. http://dx.doi.org/10.1039/c2ob25693b.

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40

Mitsui, Kazuhiko, and Jon R. Parquette. "Dendritic Amplification of Stereoselectivity of a Prolinamide-Catalyzed Direct Aldol Reaction." Israel Journal of Chemistry 49, no. 1 (2009): 119–27. http://dx.doi.org/10.1560/ijc.49.1.119.

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41

Kokotos, Christoforos G. "Construction of Tertiary Alcohols Bearing Perfluoroalkyl Chains Catalyzed by Prolinamide-Thioureas." Journal of Organic Chemistry 77, no. 2 (2012): 1131–35. http://dx.doi.org/10.1021/jo2020104.

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42

Russo, Alessio, Giovanna Botta, and Alessandra Lattanzi. "Highly stereoselective direct aldol reactions catalyzed by (S)-NOBIN-l-prolinamide." Tetrahedron 63, no. 48 (2007): 11886–92. http://dx.doi.org/10.1016/j.tet.2007.09.027.

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43

Robak, MaryAnn T., Melissa A. Herbage, and Jonathan A. Ellman. "Development of an N-sulfinyl prolinamide for the asymmetric aldol reaction." Tetrahedron 67, no. 24 (2011): 4412–16. http://dx.doi.org/10.1016/j.tet.2011.03.030.

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44

Tang, Gongkun, Xianming Hu, and Hans Josef Altenbach. "l-Prolinamide derivatives as efficient organocatalysts for aldol reactions on water." Tetrahedron Letters 52, no. 52 (2011): 7034–37. http://dx.doi.org/10.1016/j.tetlet.2011.10.009.

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45

Wang, Yongchao, Jun Lin, and Kun Wei. "Aromatic l-prolinamide-catalyzed asymmetric Michael addition of aldehydes to nitroalkenes." Tetrahedron: Asymmetry 25, no. 24 (2014): 1599–604. http://dx.doi.org/10.1016/j.tetasy.2014.11.006.

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46

Wang, Wei, Jian Wang та Hao Li. "A Simple and Efficientl-Prolinamide-Catalyzed α-Selenenylation Reaction of Aldehydes". Organic Letters 6, № 16 (2004): 2817–20. http://dx.doi.org/10.1021/ol0488946.

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47

Hara, Noriyuki, Shuichi Nakamura, Norio Shibata, and Takeshi Toru. "Enantioselective Aldol Reaction using Recyclable Montmorillonite-Entrapped N-(2-Thiophenesulfonyl)prolinamide." Advanced Synthesis & Catalysis 352, no. 10 (2010): 1621–24. http://dx.doi.org/10.1002/adsc.201000214.

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48

Gao, Jinsuo, Jian Liu, Jianting Tang, Dongmei Jiang, Bo Li, and Qihua Yang. "Chirally Functionalized Hollow Nanospheres Containing L-Prolinamide: Synthesis and Asymmetric Catalysis." Chemistry - A European Journal 16, no. 26 (2010): 7852–58. http://dx.doi.org/10.1002/chem.201000161.

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49

Kumar, Togapur Pavan, Nemali Manjula, and Kumar Katragunta. "ChemInform Abstract: Asymmetric Aldol Reactions of Isatins Catalyzed by Phthalimido-Prolinamide." ChemInform 47, no. 11 (2016): no. http://dx.doi.org/10.1002/chin.201611136.

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50

Eyckens, Daniel J., Hannah L. Brozinski, Joshua P. Delaney, Linden Servinis, Sahar Naghashian, and Luke C. Henderson. "Ion-Tagged Prolinamide Organocatalysts for the Direct Aldol Reaction On-Water." Catalysis Letters 146, no. 1 (2015): 212–19. http://dx.doi.org/10.1007/s10562-015-1630-4.

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