A multifaceted approach towards understanding the peculiar behavior of (α)-hydroxyiminophosphonates

Breakdown curves; Collision energies; E-isomers; Fragmentations pattern; Hydroxylamine derivative; Multi-faceted approach; Protonation site; Selective reduction; Tandem MS; XRD; Organic Chemistry

Abstract :

[en] The peculiar isomer-selective reduction of (α)-hydroxyiminophosphonates (oxime isomers) into (α)-hydroxyaminophosphonate (hydroxylamine) derivatives is presented. A library of 16 (α)-hydroxyiminophosphonates is prepared and studied via a unique multifaceted approach involving the interplay of NMR, XRD, MS, IM-MS and computational chemistry techniques. The combination of NMR, XRD and HPLC enables the seamless separation, identification and quantification of the oxime isomers (E/Z). Tandem MS (MS/MS) enables the determination of the fragmentation patterns for both isomers. Collision energy breakdown curves highlight the order of apparition of the fragments as well as their related energy of fragmentation, demonstrating that the strength of the C-P bond in the Z isomers is much weaker than in the E isomers. Computational chemistry demonstrates that favorable protonation site is isomer-dependent with the phosphonate moiety being the favorable protonation site for the E isomers, while protonation occurs preferentially on the amino moiety for Z isomers regardless of the phosphite source. The combination of these various methods led an unprecedented level of characterization of oxime isomers, providing a better uderstanding of the isomer-dependent behavior of (α)-hydroxyiminophosphonates. This journal is

Disciplines :

Chemistry

Author, co-author :

Toupy, Thomas ; Université de Liège - ULiège > Université de Liège - ULiège

Kune, Christopher ; Université de Liège - ULiège > Département de chimie (sciences) > Laboratoire de spectrométrie de masse (L.S.M.)

Van Hecke, Kristof ; XStruct, Department of Chemistry, Ghent University, Ghent, Belgium

Quinton, Loïc ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie biologique

Monbaliu, Jean-Christophe ; Université de Liège - ULiège > Molecular Systems (MolSys)

Language :

English

Title :

A multifaceted approach towards understanding the peculiar behavior of (α)-hydroxyiminophosphonates

Publication date :

07 January 2022

Journal title :

Organic Chemistry Frontiers

ISSN :

2052-4110

eISSN :

2052-4129

Publisher :

Royal Society of Chemistry

Volume :

Issue :

Pages :

173 - 182

Peer reviewed :

Peer Reviewed verified by ORBi

Additional URL :

http://pubs.rsc.org/en/content/articlepdf/2022/QO/D1QO01564H

Funders :

ULiège - Université de Liège
FRIA - Fonds pour la Formation à la Recherche dans l'Industrie et dans l'Agriculture
F.R.S.-FNRS - Fonds de la Recherche Scientifique
FWO - Fonds Wetenschappelijk Onderzoek Vlaanderen

Funding text :

This work was supported by the University of Liège (Welcome Grant WG-13/03, J. C. M. M.) and the F.R.S.-FNRS (Incentive grant for scientific research MIS F453020F, J. C. M. M.). Computational have been provided by the “Consortium des Équipements de Calcul Intensif” (CÉCI), funded by the “Fonds de la Recherche Scientifique de Belgique” (F.R.S.-FNRS) under Grant No. 2.5020.11. T. T. is a FRIA PhD fellow. K. V. H. thanks the Research Foundation – Flanders (FWO) (projects AUGE/11/029 and G099319N) for funding.

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Bibliography

M. Hariharan R. J. Motekaitis A. E. Martell Synthesis of dipeptides of aminophosphonic acids J. Org. Chem. 1975 40 470 473
S. J. Hecker M. D. Erion Prodrugs of Phosphates and Phosphonates J. Med. Chem. 2008 51 2328 2345
V. Kukhar and H. Hudson, Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity, John Wiley & Sons, 2000
P. R. Varga G. Keglevich Synthesis of α-Aminophosphonates and Related Derivatives; The Last Decade of the Kabachnik-Fields Reaction Molecules 2021 26 2511
G. Keglevich A. Szekrenyi Eco-Friendly Accomplishment of the Extended Kabachnik-Fields Reaction; a Solvent-and Catalyst-Free Microwave-Assisted Synthesis of α-Aminophosphonates and α-Aminophosphine Oxides Lett. Org. Chem. 2008 5 616 622
B. C. Ranu A. Hajra A simple and green procedure for the synthesis of α-aminophosphonate by a one-pot three-component condensation of carbonyl compound, amine and diethyl phosphite without solvent and catalyst Green Chem. 2002 4 551 554
X.-J. Mu M.-Y. Lei J.-P. Zou W. Zhang Microwave-assisted solvent-free and catalyst-free Kabachnik-Fields reactions for α-amino phosphonates Tetrahedron Lett. 2006 47 1125 1127
M. Zahouily A. Elmakssoudi A. Mezdar A. Rayadh S. Sebti Uncatalysed Preparation of α-Amino Phosphonates under Solvent Free Conditions J. Chem. Res. 2005 2005 324 327
I. Essid S. Touil Efficient and Green One-Pot Multi-Component Synthesis of α-Aminophosphonates Catalyzed by Zinc Triflate Curr. Org. Synth. 2017 14 272 278
M. M. Kabachnik E. V. Zobnina I. P. Beletskaya Catalyst-Free Microwave-Assisted Synthesis of α-Aminophosphonates in a Three-Component System: R1C(O)R2-(EtO)2P(O)H-RNH2Synlett 2005 2005 1393 1396
A. N. Pudovik I. V. Konovalova Addition Reactions of Esters of Phosphorus(III) Acids with Unsaturated Systems Synthesis 1979 1979 81 96
M. Ordóñez, J. L. Viveros-Ceballos and I. R. Estudillo, Amino Acid-New Insights and Roles in Plant and Animal, Stereoselective Synthesis of α-Aminophosphonic Acids through Pudovik and Kabachnik-Fields Reaction, Toshiki Asao and Md. Asaduzzaman, IntechOpen, 2017
K. R. Naidu K. R. K. Kumar Reddy C. V. Kumar C. N. Raju D. D. Sharma A facile catalyst-free Pudovik reaction for the synthesis of α-amino phosphonates S. Afr. J. Chem. 2009 62 185 188
O. I. Kolodiazhnyi S. Sheiko E. V. Grishkun C3-symmetric trialkyl phosphites as starting compounds of asymmetric synthesis Heteroat. Chem. 2000 11 138 143
F. Palacios T. K. Olszewski J. Vicario Diastereoselective hydrophosphonylation of imines using (R, R)-TADDOL phosphite. Asymmetric synthesis of α-aminophosphonic acid derivatives Org. Biomol. Chem. 2010 8 4255 4258
A. S. Demir C. Tanyeli O. Şeşenoǧlu S. Demiç O. O. Evin A simple synthesis of 1-aminophosphonic acids from 1-hydroxyiminophosphonates with NaBH4in the presence of transition metal compounds Tetrahedron Lett. 1996 37 407 410
R. Rogers M. Stern An Improved Synthesis of the Phosphonic Acid Analog of Tryptophan Synlett 1992 708
J. L. Viveros-Ceballos F. J. Sayago C. Cativiela M. Ordóñez First Practical and Efficient Synthesis of 3-Phosphorylated β-Carboline Derivatives Using the Pictet-Spengler Reaction Eur. J. Org. Chem. 2015 2015 1084 1091
J. L. Viveros-Ceballos M. Ordóñez F. J. Sayago A. I. Jiménez C. Cativiela First Synthesis of (R)-and (S,)-1,2,3,4-Tetrahydroisoquinoline-3-phosphonic Acid (TicP) Using a Pictet-Spengler Reaction Eur. J. Org. Chem. 2016 2016 2711 2719
P. Patel S. Chang N-Substituted Hydroxylamines as Synthetically Versatile Amino Sources in the Iridium-Catalyzed Mild C-H Amidation Reaction Org. Lett. 2014 16 3328 3331
E. J. Yoo S. Ma T.-S. Mei K. S. L. Chan J.-Q. Yu Pd-Catalyzed Intermolecular C-H Amination with Alkylamines J. Am. Chem. Soc. 2011 133 7652 7655
N. Matsuda K. Hirano T. Satoh M. Miura Copper-Catalyzed Direct Amination of Electron-Deficient Arenes with Hydrodryxlamines Org. Lett. 2011 13 2860 2863
L. Fan J. Hao J. Yu X. Ma J. Liu X. Luan Hydroxylamines As Bifunctional Single-Nitrogen Sources for the Rapid Assembly of Diverse Tricyclic Indole Scaffolds J. Am. Chem. Soc. 2020 142 6698 6707
E. Erdik Electrophilic α-amination of carbonyl compounds Tetrahedron 2004 60 8747 8782
M.-L. Louillat F. W. Patureau Oxidative C-H amination reactions Chem. Soc. Rev. 2014 43 901 910
Y. Park Y. Kim S. Chang Transition Metal-Catalyzed C-H Amination: Scope, Mechanism, and Applications Chem. Rev. 2017 117 9247 9301
J. Davies S. P. Morcillo J. J. Douglas D. Leonori Hydroxylamine Derivatives as Nitrogen-Radical Precursors in Visible-Light Photochemistry Chem.-Eur. J. 2018 24 12154 12163
A. El-Faham F. Albericio Synthesis and Application of N-Hydroxylamine Derivatives as Potential Replacements for HOBt Eur. J. Org. Chem. 2009 2009 1499 1501
L. Miret-Casals A. Baelo E. Julián J. Astola A. Lobo-Ruiz F. Albericio E. Torrents Hydroxylamine Derivatives as a New Paradigm in the Search of Antibacterial Agents ACS Omega 2018 3 17057 17069
N. S. Goulioukina I. A. Shergold G. N. Bondarenko M. M. Ilyin V. A. Davankov I. P. Beletskaya Palladium-Catalyzed Asymmetric Hydrogenation of N-Hydroxy-α-imino Phosphonates Using Brønsted Acid as Activator: The First Catalytic Enantioselective Approach to Chiral N-Hydroxy-α-amino Phosphonates Adv. Synth. Catal. 2012 354 2727 2733
J. Mas-Roselló C. J. Cope E. Tan B. Pinson A. Robinson T. Smejkal N. Cramer Iridium-Catalyzed Acid-Assisted Hydrogenation of Oximes to Hydroxylamines Angew. Chem., Int. Ed. 2021 60 15524 15532
H. Dollt P. Hammann S. Blechert Synthesis of (+)-(S)-Streptenol A and Biomimetic Synthesis of (2R,4S)-and (2S,4S)-2-(Pent-3-enyl)piperidin-4-ol Helv. Chim. Acta 1999 82 1111 1121
E. Breuer R. Karaman H. Leader A. Goldblum Phosphorylation of alcohols through the acid-catalysed fragmentation of α-oxyiminophosphonates J. Chem. Soc., Chem. Commun. 1987 671 672
E. Breuer R. Karaman D. Gibson H. Leader A. Goldblum α-Hydroxyiminophosphonic acids. New types of phosphorylating agents through monomeric metaphosphate J. Chem. Soc., Chem. Commun. 1988 504 506
E. Breuer R. Karaman A. Goldblum D. Gibson H. Leader B. V. L. Potter J. H. Cummins α-Oxyiminophosphonates: chemical and physical properties. Reactions, theoretical calculations, and X-ray crystal structures of (E) and (Z)-dimethyl α-hydroxyiminobenzylphosphonates J. Chem. Soc., Perkin Trans. 1 1988 3047 3057
E. Breuer M. Safadi M. Chorev A. Vineze P. Bel Synthesis and characterization of amino protected peptides derived from amino-α-hydroxyiminophosphonates Tetrahedron 1991 47 1257 1264
E. Breuer M. Mahajna Synthesis and reactions of 2,2,2-trihaloethyl α-hydroxyiminobenzylphosphonates. The influence of the ester group on the chemistry of phosphonates Heteroat. Chem. 1992 3 251 260
E. Breuer Fragmentations and Rearrangements of α-Hydroxyiminoalkylphosphonates Curr. Org. Chem. 2006 10 2357 2370
J. Katzhendler R. Karaman D. Gibson E. Breuer H. Leader Fragmentation of methyl hydrogen α-hydroxyiminophosphonates to monomeric methyl metaphosphate: stereochemistry and mechanism J. Chem. Soc., Perkin Trans. 2 1989 589 594
M. Mahajna E. Breuer 2-Cyanoethyl and p-nitrophenethyl α-hydroxyimino-and α-methoxyimino-phosphonates: potential precursors of metaphosphate anion J. Chem. Soc., Perkin Trans. 1 1994 1847 1849
J. Vicario C. Alonso J. M. de los Santos F. Palacios α-Hydroxyiminophosphonate,-phosphinate and-phosphonium Derivatives Curr. Org. Synth. 2010 7 628 649
F. W. McLafferty Tandem Mass Spectrometry Science 1981 214 280 287
C. M. Nichols J. N. Dodds B. S. Rose J. A. Picache C. B. Morris S. G. Codreanu J. C. May S. D. Sherrod J. A. McLean Untargeted Molecular Discovery in Primary Metabolism: Collision Cross Section as a Molecular Descriptor in Ion Mobility-Mass Spectrometry Anal. Chem. 2018 90 14484 14492
I. Czerwinska A. Kulesza C. Choi F. Chirot A.-L. Simon J. Far C. Kune E. de Pauw P. Dugourd Supramolecular influence on ci s-trans isomerization probed by ion mobility spectrometry Phys. Chem. Chem. Phys. 2016 18 32331 32336
A. J. Creese H. J. Cooper Separation of cis and trans Isomers of Polyproline by FAIMS Mass Spectrometry J. Am. Soc. Mass Spectrom. 2016 27 2071 2074
S. Poyer C. M. Choi C. Deo N. Bogliotti J. Xie P. Dugourd F. Chirot J.-Y. Salpin Kinetic study of azobenzene E / Z isomerization using ion mobility-mass spectrometry and liquid chromatography-UV detection Analyst 2020 145 4012 4020
X. Zheng R. S. Renslow M. M. Makola I. K. Webb L. Deng D. G. Thomas N. Govind Y. M. Ibrahim M. M. Kabanda I. A. Dubery H. M. Heyman R. D. Smith N. E. Madala E. S. Baker Structural Elucidation of cis / trans Dicaffeoylquinic Acid Photoisomerization Using Ion Mobility Spectrometry-Mass Spectrometry J. Phys. Chem. Lett. 2017 8 1381 1388
M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski and D. J Fox, Gaussian 09, Revision D.01, Gaussian, Inc., Wallingford CT, 2009
Z. Hassen A. Ben Akacha H. Zantour Synthese de Quelques α-Cetophosphonates Comportant des Hydrogenes Mobiles en Position α: Caracteristiques Spectroscopiques IR, RMN 1H, 13C, 31P et Reactivites vis-a-vis des Amines et des Derivees de L'hydrazine Phosphorus, Sulfur Silicon Relat. Elem. 2003 178 2241 2253
C. C. Tam K. L. Mattocks M. Tishler Enol-keto tautomerism of alpha-ketophosphonates Proc. Natl. Acad. Sci. U. S. A. 1981 78 3301 3304