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Статті в журналах з теми "P-Stereogenic catalysts"

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Автор: Grafiati

Опубліковано: 25 травня 2024

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1

Błaszczyk, Jarosław, Bogdan Bujnicki, Patrycja Pokora-Sobczak, Grażyna Mielniczak, Lesław Sieroń, Piotr Kiełbasiński, and Józef Drabowicz. "New Optically Active tert-Butylarylthiophosphinic Acids and Their Selenium Analogues as the Potential Synthons of Supramolecular Organometallic Complexes: Syntheses and Crystallographic Structure Determination." Molecules 28, no. 11 (May 24, 2023): 4298. http://dx.doi.org/10.3390/molecules28114298.

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Анотація:

The aim of the research described in this publication is two-fold. The first is a detailed description of the synthesis of a series of compounds containing a stereogenic heteroatom, namely the optically active P-stereogenic derivatives of tert-butylarylphoshinic acids bearing sulfur or selenium. The second is a detailed discussion dedicated to the determination of their structures by an X-ray analysis. Such a determination is needed when considering optically active hetero-oxophosphoric acids as new chiral solvating agents, precursors of new chiral ionic liquids, or ligands in complexes serving as novel organometallic catalysts.

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2

Han, Zhengxu S., Hao Wu, Bo Qu, Yuwen Wang, Ling Wu, Li Zhang, Yibo Xu, et al. "New class of P-stereogenic chiral Brønsted acid catalysts derived from chiral phosphinamides." Tetrahedron Letters 60, no. 28 (July 2019): 1834–37. http://dx.doi.org/10.1016/j.tetlet.2019.06.013.

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3

von Münchow, Tristan, Suman Dana, Yang Xu, Binbin Yuan, and Lutz Ackermann. "Enantioselective electrochemical cobalt-catalyzed aryl C–H activation reactions." Science 379, no. 6636 (March 10, 2023): 1036–42. http://dx.doi.org/10.1126/science.adg2866.

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Enantioselective redox transformations typically rely on costly transition metals as catalysts and often stoichiometric amounts of chemical redox agents as well. Electrocatalysis represents a more sustainable alternative, in particular through the use of the hydrogen evolution reaction (HER) in place of a chemical oxidant. In this work, we describe strategies for HER-coupled enantioselective aryl carbon-hydrogen bond (C–H) activation reactions using cobalt in place of a precious metal catalyst for the asymmetric oxidation. Thus, highly enantioselective carbon-hydrogen and nitrogen-hydrogen (C–H and N–H) annulations of carboxylic amides were achieved, which gave access to point and axially chiral compounds. Furthermore, the cobalt-mediated electrocatalysis enabled the preparation of various phosphorus (P)–stereogenic compounds by selective desymmetrization through dehydrogenative C–H activation reactions.

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4

Chan, Vincent S., Melanie Chiu, Robert G. Bergman, and F. Dean Toste. "Development of Ruthenium Catalysts for the Enantioselective Synthesis of P-Stereogenic Phosphines via Nucleophilic Phosphido Intermediates." Journal of the American Chemical Society 131, no. 16 (April 29, 2009): 6021–32. http://dx.doi.org/10.1021/ja9014887.

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5

Gladiali, Serafino, Serenella Medici, Giovanna Pirri, Sonia Pulacchini, and Davide Fabbri. "BINAPS - An axially chiral P,S-heterodonor ligand for asymmetric catalysis based on binaphthalene backbone." Canadian Journal of Chemistry 79, no. 5-6 (May 1, 2001): 670–78. http://dx.doi.org/10.1139/v01-041.

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Анотація:

The chelating P,S-heterodonor ligand 2-diphenylphosphanyl-1,1'-binaphthalene-2'-thiol (11) (BINAPS), which features a chiral axis as the unique stereogenic element, has been prepared in both racemic and enantiopure form through a multistep reaction sequence using 2,2'-dihydroxy-1,1'-binaphthalene (BINOL) as the starting material. The reaction sequence is completely stereoconservative and (S)-11 is obtained with no loss of enantiopurity from pure (S)-BINOL. (R)-11 can be alternatively obtained by resolution of racemic 11 using the chiral (S)-benzylaminato Pd(II)-complex 19 as the resolving agent. The S-methyl or the S-i-propyl derivatives 14 have been used as chiral ligands in the Rh(I)-catalyzed asymmetric hydroformylation of styrene and in the hydrogen transfer reduction of acetophenone with modest success (up to 20% ee). In the presence of suitable Pd-complexes the same ligands provide higher ees in the hydrosilylation of styrene (50% ee) and in the allylic alkylation of 1,3-diphenylprop-2-enyl acetate (60% ee).Key words: heterodonor ligands, binaphthalene derivatives, enantioselective catalysis, transition metal catalysts, allylic alkylation.

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6

Biosca, Maria, Ernest Salomó, Pol de la Cruz-Sánchez, Antoni Riera, Xavier Verdaguer, Oscar Pàmies, and Montserrat Diéguez. "Extending the Substrate Scope in the Hydrogenation of Unfunctionalized Tetrasubstituted Olefins with Ir-P Stereogenic Aminophosphine–Oxazoline Catalysts." Organic Letters 21, no. 3 (January 16, 2019): 807–11. http://dx.doi.org/10.1021/acs.orglett.8b04084.

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7

Bagi, Péter, Réka Herbay, Gábor Györke, Péter Pongrácz, László Kollár, István Timári, László Drahos, and György Keglevich. "Preparation of Palladium(II) Complexes of 1-substituted-3-phospholene Ligands and their Evaluation as Catalysts in Hydroalkoxycarbonylation." Current Organic Chemistry 23, no. 25 (January 14, 2020): 2873–79. http://dx.doi.org/10.2174/1385272823666191204151311.

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: A series of palladium(II) complexes incorporating 1-substituted-3-methyl-3- phospholenes as the P-ligands were prepared from phospholene oxides by deoxygenation followed by complexation with PdCl2(PhCN)2. The two 1-substituted-3-methyl-3- phospholene ligands were trans position to each other in the Pd(II)-complexes. As the ligands contain a P-stereogenic center, the Pd-complexes were obtained as a 1:1 mixture of two stereoisomers, the homochiral (R,R and S,S) and the meso (R,S) forms, when racemic starting materials were used. An optically active Pd-complex containing (R)-1-propyl- 3-phospholene ligand was also prepared. Catalytic activity of an aryl- and an alkyl-3- phospholene-palladium(II)-complex was evaluated in hydroalkoxycarbonylation of styrene. The alkyl-derivative showed higher activity and selectivity towards the formation of the esters of 3-phenylpropionic acid. However, the overall activity of these PdCl2(phospholene)2-type complexes was low.

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8

Huber, Raffael, Alessandro Passera, Erik Gubler, and Antonio Mezzetti. "P-Stereogenic PN(H)P Iron(II) Catalysts for the Asymmetric Hydrogenation of Ketones: The Importance of Non-Covalent Interactions in Rational Ligand Design by Computation." Advanced Synthesis & Catalysis 360, no. 15 (June 22, 2018): 2900–2913. http://dx.doi.org/10.1002/adsc.201800433.

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9

Numan, Ahmed, and Matthew Brichacek. "Asymmetric Synthesis of Stereogenic Phosphorus P(V) Centers Using Chiral Nucleophilic Catalysis." Molecules 26, no. 12 (June 15, 2021): 3661. http://dx.doi.org/10.3390/molecules26123661.

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Анотація:

Organophosphates have been widely used in agrochemistry, as reagents for organic synthesis, and in biochemistry. Phosphate mimics possessing four unique substituents, and thereby a chirality center, are useful in transition metal catalysis and as nucleotide therapeutics. The catalytic, stereocontrolled synthesis of phosphorus-stereogenic centers is challenging and traditionally depends on a resolution or use of stochiometric auxiliaries. Herein, enantioenriched phosphorus centers have been synthesized using chiral nucleophilic catalysis. Racemic H-phosphinate species were coupled with nucleophilic alcohols under halogenating conditions. Chiral phosphonate products were synthesized in acceptable yields (33–95%) and modest enantioselectivity (up to 62% ee) was observed after identification of an appropriate chiral catalyst and optimization of the solvent, base, and temperature. Nucleophilic catalysis has a tremendous potential to produce enantioenriched phosphate mimics that could be used as prodrugs or chemical biology probes.

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10

Funk, Michael A. "A P catalyst for stereogenic P(III)." Science 371, no. 6530 (February 11, 2021): 687.5–687. http://dx.doi.org/10.1126/science.371.6530.687-e.

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11

Xiang, Yijun, Qianyi Ge, Shulei Wu, Xing Zheng, and Zehua Yang. "Synthesis and application in asymmetric catalysis of P-stereogenic pincer–metal complexes." RSC Advances 10, no. 16 (2020): 9563–78. http://dx.doi.org/10.1039/d0ra00377h.

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12

Xie, Xiaoxiao, Sanliang Li, Qiaoyu Chen, Hao Guo, Junfeng Yang, and Junliang Zhang. "Synthesis and application of novel P-chiral monophosphorus ligands." Organic Chemistry Frontiers 9, no. 6 (2022): 1589–92. http://dx.doi.org/10.1039/d1qo01819a.

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Анотація:

A series of novel P-stereogenic monophosphorus ligands (Xie-phos) were synthesized via the hydrophosphinylation of alkynes with secondary phosphine oxides by palladium catalysis and the following base mediated cyclization.

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13

Schwenk, R., and A. Togni. "P-Trifluoromethyl ligands derived from Josiphos in the Ir-catalysed hydrogenation of 3,4-dihydroisoquinoline hydrochlorides." Dalton Transactions 44, no. 45 (2015): 19566–75. http://dx.doi.org/10.1039/c5dt02019k.

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14

Rojo, Pep, Antoni Riera, and Xavier Verdaguer. "Bulky P-stereogenic ligands. A success story in asymmetric catalysis." Coordination Chemistry Reviews 489 (August 2023): 215192. http://dx.doi.org/10.1016/j.ccr.2023.215192.

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15

Nagel, Ulrich, and Christoph Roller. "Enantioselektive Katalyse, XVIII Der Einfluß nicht koordinierter Stereozentren auf die enantioselektive Hydrierung/Enantioselective Catalysis, XVIII The Influence of Non-Coordinated Stereocenters on the Enantioselective Hydrogenation." Zeitschrift für Naturforschung B 53, no. 2 (February 1, 1998): 211–23. http://dx.doi.org/10.1515/znb-1998-0213.

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Abstract 3,4-Bis{[2-(methyl-phenyl-oxophosphanyl)-ethyl]phenyl-phosphanyl}pyrrolidines have been synthesized by Michael Addition from the corresponding methyl-phenyl-vinyl-phosphane oxides and 3,4-bis(phenylphosphino)pyrrolidines. For purification of the ligands palladium complexes were used and with the enantiomerically pure ligands Rh complexes have been prepared. The catalyst has 6 stereogenic centers. In the hydrogenation of Z-α-acetamidocinnamic acid all six stereogenic centers have an influence on the enantioselectivity. The influence is strongest from the C stereocenters of the pyrrolidine ring. Less important are the stereogenic centers on the coordinated P atoms. The influence of the stereocenters on the non-coordinated P = O groups is the least, but it is not negligible. The ee values obtained with the ligands containing P = O groups are much lower than those obtained with ligands which are substituted only with aryl groups. Ketones are hydrogenated with only low ee’s.

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16

Grabulosa, Arnald, Alberto Mannu, Guillermo Muller, Teresa Calvet, and Mercè Font-Bardia. "P-Stereogenic monophosphines in Pd-catalysed enantioselective hydrovinylation of styrene." Journal of Organometallic Chemistry 696, no. 11-12 (June 2011): 2338–45. http://dx.doi.org/10.1016/j.jorganchem.2011.02.034.

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17

Ramazanova, Kyzgaldak, Soumyadeep Chakrabortty, Bernd H. Müller, Peter Lönnecke, Johannes G. de Vries, and Evamarie Hey-Hawkins. "Synthesis of P-stereogenic 1-phosphanorbornane-derived phosphine–phosphite ligands and application in asymmetric catalysis." RSC Advances 13, no. 49 (2023): 34439–44. http://dx.doi.org/10.1039/d3ra07630j.

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Анотація:

A convenient synthesis of enantiopure mixed donor phosphine–phosphite ligands has been developed incorporating P-stereogenic phosphanorbornane and axially chiral bisnaphthols into one ligand structure.

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18

Álvarez-Yebra, Rubén, Pep Rojo, Antoni Riera, and Xavier Verdaguer. "Iridium complexes with P-stereogenic phosphino imidazole ligands: Synthesis, structure and catalysis." Tetrahedron 75, no. 32 (August 2019): 4358–64. http://dx.doi.org/10.1016/j.tet.2019.04.032.

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19

Zhang, Jieming, Hang Ni, Qi Wu, Junfeng Yang, and Junliang Zhang. "Development of P, S and Si-Stereogenic Compounds Synthesis via Palladium Catalysis." Chinese Journal of Organic Chemistry 42, no. 10 (2022): 3118. http://dx.doi.org/10.6023/cjoc202208043.

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20

Sondenecker, Aline, Ján Cvengroš, Raphael Aardoom, and Antonio Togni. "P-Stereogenic Ferrocene-Based (Trifluoromethyl)phosphanes: Synthesis, Structure, Coordination Properties and Catalysis." European Journal of Organic Chemistry 2011, no. 1 (November 12, 2010): 78–87. http://dx.doi.org/10.1002/ejoc.201001162.

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21

Han, Zhengxu S., Li Zhang, Yibo Xu, Joshua D. Sieber, Maurice A. Marsini, Zhibin Li, Jonathan T. Reeves, et al. "Efficient Asymmetric Synthesis of Structurally Diverse P-Stereogenic Phosphinamides for Catalyst Design." Angewandte Chemie International Edition 54, no. 18 (March 10, 2015): 5474–77. http://dx.doi.org/10.1002/anie.201500350.

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22

Han, Zhengxu S., Li Zhang, Yibo Xu, Joshua D. Sieber, Maurice A. Marsini, Zhibin Li, Jonathan T. Reeves, et al. "Efficient Asymmetric Synthesis of Structurally Diverse P-Stereogenic Phosphinamides for Catalyst Design." Angewandte Chemie 127, no. 18 (March 10, 2015): 5564–67. http://dx.doi.org/10.1002/ange.201500350.

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23

Berger, Olivier, and Jean-Luc Montchamp. "A General Strategy for the Synthesis of P-Stereogenic Compounds." Angewandte Chemie International Edition 52, no. 43 (September 9, 2013): 11377–80. http://dx.doi.org/10.1002/anie.201306628.

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24

Balkaner, Orçun, Derya Işıl Sarıoğulları, and Aylin Uslu. "A synthetic strategy of P-stereogenic ligands for catalysis: Examples based on cyclotriphosphazenes." Journal of Molecular Structure 1261 (August 2022): 132834. http://dx.doi.org/10.1016/j.molstruc.2022.132834.

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25

Cabré, Albert, Antoni Riera, and Xavier Verdaguer. "P-Stereogenic Amino-Phosphines as Chiral Ligands: From Privileged Intermediates to Asymmetric Catalysis." Accounts of Chemical Research 53, no. 3 (February 27, 2020): 676–89. http://dx.doi.org/10.1021/acs.accounts.9b00633.

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26

Harvey, James Stephen, and Véronique Gouverneur. "Catalytic enantioselective synthesis of P-stereogenic compounds." Chemical Communications 46, no. 40 (2010): 7477. http://dx.doi.org/10.1039/c0cc01939a.

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27

Dziuba, Kamil, Małgorzata Lubańska, and K. Michał Pietrusiewicz. "Enantiodivergent Synthesis of Both PAMPO Enantiomers Using l-Menthyl Chloroacetate and Stereomutation at P in Classical Quaternisation Reactions." Synthesis 52, no. 06 (December 4, 2019): 909–16. http://dx.doi.org/10.1055/s-0039-1691531.

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Анотація:

A practical protocol for efficient synthesis of both PAMPO enantiomers as well as related functionalised P-stereogenic phosphine oxides in 1–3 steps from effectively resolved (S P)-l-menthyl o-anisyl-(phenyl)phosphinylacetate has been developed. Examples of non-stereoselective quaternisation of a tertiary phosphine by alkyl halides have been revealed.

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28

Vinokurov, Nikolai, K. Michał Pietrusiewicz, Sławomir Frynas, Michael Wiebcke, and Holger Butenschön. "Asymmetric 1,3-dipolar cycloaddition with a P-stereogenic dipolarophile: An efficient approach to novel P-stereogenic 1,2-diphosphine systems." Chemical Communications, no. 42 (2008): 5408. http://dx.doi.org/10.1039/b810573a.

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29

Whittaker, Benjamin, Manuel de Lera Ruiz, and Christopher J. Hayes. "Stereoselective synthesis of highly functionalised P-stereogenic nucleosides via palladium-catalysed P–C cross-coupling reactions." Tetrahedron Letters 49, no. 49 (December 2008): 6984–87. http://dx.doi.org/10.1016/j.tetlet.2008.09.102.

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30

Buergler, Jonas F., Katrin Niedermann, and Antonio Togni. "P-Stereogenic Trifluoromethyl Derivatives of Josiphos: Synthesis, Coordination Properties, and Applications in Asymmetric Catalysis." Chemistry - A European Journal 18, no. 2 (December 8, 2011): 632–40. http://dx.doi.org/10.1002/chem.201102390.

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31

Schmitz, Christian, Walter Leitner, and Giancarlo Franciò. "Synthesis of P-Stereogenic Phosphoramidite and Phosphorodiamidite Ligands and Their Application in Asymmetric Catalysis." European Journal of Organic Chemistry 2015, no. 28 (August 12, 2015): 6205–30. http://dx.doi.org/10.1002/ejoc.201500767.

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32

Han, Zhengxu S., and et al. "ChemInform Abstract: Efficient Asymmetric Synthesis of Structurally Diverse P-Stereogenic Phosphinamides for Catalyst Design." ChemInform 46, no. 36 (August 20, 2015): no. http://dx.doi.org/10.1002/chin.201536217.

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33

Mutlu, Ömer Faruk, Arzu Binici, Aytuğ Okumuş, Gamze Elmas, Bünyemin Çoşut, Zeynel Kılıç, and Tuncer Hökelek. "Phosphorus–nitrogen compounds. Part 54. syntheses of chiral amino-4-fluorobenzyl-spiro(N/O)cyclotriphosphazenes: structural and stereogenic properties." New Journal of Chemistry 45, no. 27 (2021): 12178–92. http://dx.doi.org/10.1039/d1nj00934f.

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Syntheses, spectral and crystallographic characterizations and stereogenic properties by ³¹P NMR spectra recorded with the addition of CSA, CD spectra and chiral HPLC of amino-4-fluorobenzylspiro(N/O)cyclotriphosphazenes were examined.

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34

Imoto, Hiroaki, Yasuhiro Morisaki, and Yoshiki Chujo. "Synthesis and coordination behaviors of P-stereogenic polymers." Chemical Communications 46, no. 40 (2010): 7542. http://dx.doi.org/10.1039/c0cc03120h.

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35

Dorta, Romano, Alberto Herrera, Anthony Linden, Frank Heinemann, René-Chris Brachvogel, and Max von Delius. "Optimized Syntheses of Optically Pure P-Alkene Ligands: Crystal Structures of a Pair of P-Stereogenic Diastereomers." Synthesis 48, no. 08 (February 17, 2016): 1117–21. http://dx.doi.org/10.1055/s-0035-1560410.

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36

Join, Benoît, David Mimeau, Olivier Delacroix, and Annie-Claude Gaumont. "Pallado-catalysed hydrophosphination of alkynes: access to enantio-enriched P-stereogenic vinyl phosphine–boranes." Chem. Commun., no. 30 (2006): 3249–51. http://dx.doi.org/10.1039/b607434k.

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37

Christ, M. Lorraine, Maria Zablocka, Sally Spencer, Rebecca J. Lavender, Marc Lemaire та Jean Pierre Majoral. "Cyclic β-iminophosphine: New P-stereogenic ligand for the asymmetric catalysed hydrogenation of ketones". Journal of Molecular Catalysis A: Chemical 245, № 1-2 (лютий 2006): 210–16. http://dx.doi.org/10.1016/j.molcata.2005.09.043.

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38

Clavero, Pau, Arnald Grabulosa, Mercè Font-Bardia, and Guillermo Muller. "P-Stereogenic monophosphines with the 2-p-terphenylyl and 1-pyrenyl substituents. Application to Pd and Ru asymmetric catalysis." Journal of Molecular Catalysis A: Chemical 391 (September 2014): 183–90. http://dx.doi.org/10.1016/j.molcata.2014.04.026.

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39

Schmitz, Christian, Walter Leitner, and Giancarlo Francio. "ChemInform Abstract: Synthesis of P-Stereogenic Phosphoramidite and Phosphorodiamidite Ligands and Their Application in Asymmetric Catalysis." ChemInform 47, no. 7 (January 2016): no. http://dx.doi.org/10.1002/chin.201607021.

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40

Clarke, Eoin F., Eoin Rafter, Helge Müller-Bunz, Lee J. Higham, and Declan G. Gilheany. "The synthesis of P-stereogenic MOP analogues and their use in rhodium catalysed asymmetric addition." Journal of Organometallic Chemistry 696, no. 23 (November 2011): 3608–15. http://dx.doi.org/10.1016/j.jorganchem.2011.08.010.

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41

Nishida, Goushi, Keiichi Noguchi, Masao Hirano, and Ken Tanaka. "Enantioselective Synthesis of P-Stereogenic Alkynylphosphine Oxides by Rh-Catalyzed [2+2+2] Cycloaddition." Angewandte Chemie International Edition 47, no. 18 (April 21, 2008): 3410–13. http://dx.doi.org/10.1002/anie.200800144.

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42

Vinokurov, Nikolai, K. Michal Pietrusiewicz, and Holger Butenschön. "Asymmetric Diels–Alder cycloaddition of a di-P-stereogenic dienophile with cyclopentadiene." Tetrahedron: Asymmetry 20, no. 9 (May 2009): 1081–85. http://dx.doi.org/10.1016/j.tetasy.2009.03.022.

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43

Reichl, Kyle D., Daniel H. Ess, and Alexander T. Radosevich. "Catalyzing Pyramidal Inversion: Configurational Lability of P-Stereogenic Phosphines via Single Electron Oxidation." Journal of the American Chemical Society 135, no. 25 (June 17, 2013): 9354–57. http://dx.doi.org/10.1021/ja404943x.

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44

Bergin, Enda, Cormac T. O'Connor, Shane B. Robinson, Eoghan M. McGarrigle, Colm P. O'Mahony, and Declan G. Gilheany. "Synthesis of P-Stereogenic Phosphorus Compounds. Asymmetric Oxidation of Phosphines under Appel Conditions." Journal of the American Chemical Society 129, no. 31 (August 2007): 9566–67. http://dx.doi.org/10.1021/ja072925l.

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45

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Granander, Johan, Francesco Secci, Peter O’Brien, and Brian Kelly. "Kinetic resolution of P-stereogenic phosphine boranes via deprotonation using s-butyllithium/(−)-sparteine." Tetrahedron: Asymmetry 20, no. 21 (November 2009): 2432–34. http://dx.doi.org/10.1016/j.tetasy.2009.10.026.

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Moulin, Dominique, Sébastien Bago, Christophe Bauduin, Christophe Darcel, and Sylvain Jugé. "Asymmetric synthesis of P-stereogenic o-hydroxyaryl-phosphine (borane) and phosphine-phosphinite ligands." Tetrahedron: Asymmetry 11, no. 19 (October 2000): 3939–56. http://dx.doi.org/10.1016/s0957-4166(00)00372-4.

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Williams, B. Scott, Paulo Dani, Martin Lutz, Anthony L Spek, and Gerard van Koten. "Development of the First P-Stereogenic PCP Pincer Ligands, Their Metallation by Palladium and Platinum, and Preliminary Catalysis." Helvetica Chimica Acta 84, no. 11 (November 14, 2001): 3519–30. http://dx.doi.org/10.1002/1522-2675(20011114)84:11<3519::aid-hlca3519>3.0.co;2-9.

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