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Journal articles on the topic 'P-Stereogenic catalysts'

Author: Grafiati

Published: 25 May 2024

Last updated: 31 July 2025

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1

Błaszczyk, Jarosław, Bogdan Bujnicki, Patrycja Pokora-Sobczak, et al. "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 (2023): 4298. http://dx.doi.org/10.3390/molecules28114298.

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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 servin

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2

Han, Zhengxu S., Hao Wu, Bo Qu, et al. "New class of P-stereogenic chiral Brønsted acid catalysts derived from chiral phosphinamides." Tetrahedron Letters 60, no. 28 (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 (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–

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4

Császár, Zsófia, Mária Guóth, Margit Kovács, Attila C. Bényei, József Bakos, and Gergely Farkas. "Asymmetric Hydrogenation of Ketones by Simple Alkane-Diyl-Based Ir(P,N,O) Catalysts: A Comparative Study." Molecules 29, no. 16 (2024): 3743. http://dx.doi.org/10.3390/molecules29163743.

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The development of new chiral ligands with simple and modular structure represents a challenging direction in the design of efficient homogeneous transition metal catalysts. Herein, we report on the asymmetric hydrogenation of prochiral ketones catalyzed by the iridium complexes of simple alkane-diyl-based P,N,O-type chiral ligands with a highly modular structure. The role of (i) the P-N and N-O backbone in the potentially tridentate ligands, (ii) the number, position and relative configuration of their stereogenic elements and (iii) the effect of their NH and OH subunits on the activity and e

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5

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 (2009): 6021–32. http://dx.doi.org/10.1021/ja9014887.

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6

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 (2001): 670–78. http://dx.doi.org/10.1139/v01-041.

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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 agen

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7

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

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8

Bagi, Péter, Réka Herbay, Gábor Györke, et al. "Preparation of Palladium(II) Complexes of 1-substituted-3-phospholene Ligands and their Evaluation as Catalysts in Hydroalkoxycarbonylation." Current Organic Chemistry 23, no. 25 (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-phospho

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9

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 (2018): 2900–2913. http://dx.doi.org/10.1002/adsc.201800433.

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10

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

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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 nucleoph

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11

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

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12

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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13

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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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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14

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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15

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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16

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 (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 pyrrol

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17

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 (2011): 2338–45. http://dx.doi.org/10.1016/j.jorganchem.2011.02.034.

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18

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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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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19

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 (2019): 4358–64. http://dx.doi.org/10.1016/j.tet.2019.04.032.

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20

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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21

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 (2010): 78–87. http://dx.doi.org/10.1002/ejoc.201001162.

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22

Han, Zhengxu S., Li Zhang, Yibo Xu, et al. "Efficient Asymmetric Synthesis of Structurally Diverse P-Stereogenic Phosphinamides for Catalyst Design." Angewandte Chemie International Edition 54, no. 18 (2015): 5474–77. http://dx.doi.org/10.1002/anie.201500350.

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23

Han, Zhengxu S., Li Zhang, Yibo Xu, et al. "Efficient Asymmetric Synthesis of Structurally Diverse P-Stereogenic Phosphinamides for Catalyst Design." Angewandte Chemie 127, no. 18 (2015): 5564–67. http://dx.doi.org/10.1002/ange.201500350.

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24

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

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25

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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26

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 (2020): 676–89. http://dx.doi.org/10.1021/acs.accounts.9b00633.

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27

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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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

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 (2019): 909–16. http://dx.doi.org/10.1055/s-0039-1691531.

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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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30

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 (2008): 6984–87. http://dx.doi.org/10.1016/j.tetlet.2008.09.102.

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31

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 (2011): 632–40. http://dx.doi.org/10.1002/chem.201102390.

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32

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 (2015): 6205–30. http://dx.doi.org/10.1002/ejoc.201500767.

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33

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

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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

Mutlu, Ömer Faruk, Arzu Binici, Aytuğ Okumuş, et al. "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 <sup>31</sup>P 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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36

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 (2016): 1117–21. http://dx.doi.org/10.1055/s-0035-1560410.

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37

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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38

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 (2006): 210–16. http://dx.doi.org/10.1016/j.molcata.2005.09.043.

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39

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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40

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 (2016): no. http://dx.doi.org/10.1002/chin.201607021.

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41

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 (2011): 3608–15. http://dx.doi.org/10.1016/j.jorganchem.2011.08.010.

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42

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 (2008): 3410–13. http://dx.doi.org/10.1002/anie.200800144.

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43

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 (2009): 1081–85. http://dx.doi.org/10.1016/j.tetasy.2009.03.022.

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44

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 (2013): 9354–57. http://dx.doi.org/10.1021/ja404943x.

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45

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 (2007): 9566–67. http://dx.doi.org/10.1021/ja072925l.

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46

Huang, Zhijian, Xuan Huang, Baosheng Li, et al. "Access to P-Stereogenic Phosphinates via N-Heterocyclic Carbene-Catalyzed Desymmetrization of Bisphenols." Journal of the American Chemical Society 138, no. 24 (2016): 7524–27. http://dx.doi.org/10.1021/jacs.6b04624.

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47

Glueck, David S. "Catalytic Asymmetric Synthesis of P-Stereogenic Phosphines: Beyond Precious Metals." Synlett, October 13, 2020. http://dx.doi.org/10.1055/s-0040-1707309.

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AbstractMetal-catalyzed asymmetric synthesis of P-stereogenic phosphines is a potentially useful approach to a class of chiral ligands with valuable applications in asymmetric catalysis. We introduced this idea with chiral platinum and palladium catalysts, exploiting rapid pyramidal inversion in diastereomeric metal–phosphido complexes (ML*(PRR′)) to control phosphorus stereochemistry. This Account summarizes our attempts to develop related synthetic methods using earth-abundant metals, especially copper, in which weaker metal–ligand bonds and faster substitution processes were expected to res

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48

Pramanik, Milan, Michael Guerzoni, Emma Richards, and Rebecca Melen. "Recent Advances in Asymmetric Catalysis Using p‐Block Elements." Angewandte Chemie International Edition, December 2023. http://dx.doi.org/10.1002/anie.202316461.

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Abstract: The development of new methods for enantioselective reactions that generate stereogenic centres within molecules are a cornerstone of organic synthesis. Typically, metal catalysts bearing chiral ligands as well as chiral organocatalysts have been employed for the enantioselective synthesis of organic compounds. In this review, we highlight the recent advances in the main group catalysis for enantioselective reactions using the p‐block elements (boron, aluminium, phosphorus, bismuth) as a complementary and sustainable approach to generate chiral molecules. Several of these catalysts b

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49

Pramanik, Milan, Michael Guerzoni, Emma Richards, and Rebecca Melen. "Recent Advances in Asymmetric Catalysis Using p‐Block Elements." Angewandte Chemie, December 2023. http://dx.doi.org/10.1002/ange.202316461.

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Abstract: The development of new methods for enantioselective reactions that generate stereogenic centres within molecules are a cornerstone of organic synthesis. Typically, metal catalysts bearing chiral ligands as well as chiral organocatalysts have been employed for the enantioselective synthesis of organic compounds. In this review, we highlight the recent advances in the main group catalysis for enantioselective reactions using the p‐block elements (boron, aluminium, phosphorus, bismuth) as a complementary and sustainable approach to generate chiral molecules. Several of these catalysts b

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50

Kang, Jie, Simu Ren, and Bo Su. "Synthesis of P-Chiral Tertiary Phosphine Oxides by the Copper-Catalyzed Dynamic Kinetic Asymmetric C-P Cross-Coupling." Synlett, July 11, 2023. http://dx.doi.org/10.1055/a-2127-1305.

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P-stereogenic phosphorus compounds are of importance in various areas. Some strategies have been developed for the enantioselective formation of C-P bonds, among which transition metal-catalyzed asymmetric C-P cross-coupling of secondary phosphine oxides (SPOs)—bench-stable, odorless, and nontoxic—is more appealing. Due to the elusive racemization of SPOs, reactions with them usually proceed in a kinetic resolution fashion, thus being less practical. Highlighted here is a copper-catalyzed highly enantioselective dynamic kinetic intermolecular C-P coupling of SPOs and aryl iodides. The successf

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