 | Dr. Boris Maryasin University of Vienna Institute of Theoretical Chemistry Währinger Str. 17 1090 Vienna Austria boris.maryasin@univie.ac.at +43 1 4277 52763 RID: P-3000-2016 ORCID: 0000-0001-7943-7333 Google Scholar: ho_iIhQAAAAJ |
| Focus Area |
| We clarify the mechanisms of organic transformations and predict the reaction outcomes, such as regio- and enantioselectivity, using modern quantum chemical approaches. The close collaborations with synthetic organic chemists allow us to verify and test our predictions. Our aim is to improve the efficiency of the experiments with theoretical studies. |
| Awards & Prizes |
|
| Publications |
Computational Insights into the Mechanism of Lewis Acid-Catalyzed Alkene-Aldehyde Coupling ChemPlusChem, (accepted), (2025), DOI: 10.1002/cplu.202400751 47. M. Lemmerer, V. Tona, D. Just, M. Vavrík, B. Maryasin, G. Di Mauro, A. B. zur Bonsen, D. Kaiser, N. Maulide Iodide Anion Enables a Reductive Cross-electrophile Coupling for Preparing Tertiary Amines Angew. Chem. Int. Ed., (in press), (2024), DOI: 10.1002/anie.202409688 46. K. Song, R. Meyrelles, G. Pilet, B. Maryasin, M. Médebielle, J. Merad Dication Disulfuranes as Photoactivatable Sources of Radical Organocatalysts Angew. Chem. Int. Ed. , (in press), (2024), DOI: 10.1002/anie.202419751 45. A. Preinfalk, R. Oost, M. Menger, M. Simaan, S. Lemouzy, S. Senoner, S. Shaaban, L. González, B. Maryasin, N. Maulide Enantioconvergent Negishi Cross-couplings of Racemic Secondary Organozinc Reagents to Access Privileged Scaffolds: a Combined Experimental and Theoretical Study Angew. Chem. 63, e202414868, (2024), DOI: 10.1002/anie.202414868 44. R. Tinelli, M. Schupp, I. Klose, S. Shaaban, B. Maryasin, L. González, N. Maulide Diastereoselective Hydride Transfer Enables a Synthesis of Chiral 1,5-Carboxamido-Trifluoromethylcarbinols Chem. Sci. 15, 15751-15756 , (2024), DOI: 10.1039/D4SC05049E 43. N. Gillaizeau-Simonian, P. Spieß, M. Riomet, B. Maryasin, I. Klose, A. Beaton Garcia, L. Pollesböck, D. Kaldre, U. Todorovic, J. Minghua Liu, D. Kaiser, L. González, N. Maulide Stereodivergent Synthesis of 1,4-Dicarbonyl Compounds through Sulfonium Rearrangement: Mechanistic Investigation, Stereocontrolled Access to γ-Lactones and γ-Lactams and Total Synthesis of Paraconic Acids J. Am. Chem. Soc. 146, 13914-13923, (2024), DOI: 10.1021/jacs.4c01755 42. F. Calcagno, B. Maryasin, M. Garavelli, D. Avagliano, I. Rivalta Modeling Solvent Effects and Convergence of 31P-NMR Shielding Calculations with COBRAMM J. Comput. Chem. 45, 1562-1575, (2024), DOI: 10.1002/jcc.27338 41. J. Hipólito, R. Meyrelles, B. Maryasin, L. G. Alves, A. M. Martins Reactions of Heteroallenes with Salan-based Ti(IV) Complexes: A Joint Experimental and Computational Study Chem. Asian J. , e202400165, (2024), DOI: 10.1002/asia.202400165 40. T. Krivobokova, G. Finocchio, B. Maryasin Factorizing Yields in Buchwald-Hartwig Amination (submitted), (2023) T. Krivobokova, G. Finocchio, B. Maryasin Mechanistic Study on Selenium- and Sulfur-Mediated Isomerization of Hydroxamic Acids Chem. - Eur. J. 29, e202302386, (2023), DOI: 10.1002/chem.202302386 38. G. Archer, R. Meyrelles, I. Eder, N. Kovács, B. Maryasin, M. Médebielle, J. Merad Photoredox-Catalyzed α-C-H Monoalkylation of Symmetric Polyols in the Presence of CO2 Angew. Chem. Int. Ed. , e202315329, (2023), DOI: 10.1002/anie.202315329 G. Archer, R. Meyrelles, I. Eder, N. Kovács, B. Maryasin, M. Médebielle, J. Merad Mechanistic Study on Selenium- and Sulfur-mediated Isomerisation of Hydroxamic Acids Chem. Eur. J. , e202302386, (2023), DOI: 10.1002/chem.202302386 36. P. S. Grant, R. Meyrelles, O. Gajsek, G. Niederacher, B. Maryasin, N. Maulide Biomimetic Cationic Cyclopropanation Enables an Efficient Chemoenzymatic Synthesis of 6,8-Cycloeudesmanes J. Am. Chem. Soc. 145, 5855–5863, (2023), DOI: 10.1021/jacs.2c13116 35. M. Feng, R. Tinelli, R. Meyrelles, L. González, B. Maryasin, N. Maulide Direct Synthesis of α-Amino Acid Derivatives via Hydrative Amination of Alkynes Angew. Chem. Int. Ed. 62, e202212399, (2022), DOI: 10.1002/anie.202212399 34. G. Huang, R. Guillot, C. Kouklovsky, B. Maryasin, A. de la Torre Diastereo- and Enantioselective Inverse-Electron-Demand Diels–Alder Cycloaddition between 2-Pyrones and Acyclic Enol Ethers Angew. Chem. Int. Ed. 61, e202208185, (2022), DOI: 10.1002/anie.202208185 G. Huang, R. Guillot, C. Kouklovsky, B. Maryasin, A. de la Torre Deployment of Sulfinimines in Charge-Accelerated Sulfonium Rearrangement Enables a Surrogate Asymmetric Mannich Reaction J. Am. Chem. Soc. 144, 13044–13049, (2022), DOI: 10.1021/jacs.2c05368 32. J. Merad, P. Grant, T. Stopka, J. Sabbatani, R. Meyrelles, A. Preinfalk, J. Matyasovsky, B. Maryasin, L. González, N. Maulide Direct Stereodivergent Olefination of Carbonyl Compounds with Sulfur Ylides J. Am. Chem. Soc. 144, 12536–12543, (2022), DOI: 10.1021/jacs.2c05637 31. M. Lunzer, B. Maryasin, T. Zandrini, S. Baudis, A. Ovsianikov, R. Liska A Disulfide-Based Linker for Thiol-Norbornene Conjugation: Formation and Cleavage of Hydrogels by the use of Light J. Am. Chem. Soc. 13, 1158-1168, (2022), DOI: 10.1039/D1PY00914A 30. M. Lemmerer, M. Riomet, R. Meyrelles, B. Maryasin, L. González, N. Maulide HFIP Mediates a Direct C-C Coupling Between Michael Acceptors and Eschenmoser's Salt Angew. Chem. Int. Ed. 61, e202109933, (2022), DOI: 10.1002/anie.202109933 M. Lemmerer, M. Riomet, R. Meyrelles, B. Maryasin, L. González, N. Maulide Computational Investigation of the Aza-Cope Rearrangement Leading to Angularly Substituted 1-Azabicyclic Rings Synlett , , (2022), DOI: 10.1055/a-1946-6578 28. S. Amthor, D. Hernández-Castillo, B. Maryasin, P. Seeber, A. K. Mengele, S. Gräfe, L. González, S. Rau Strong Ligand Stabilization Based on π–Extension in a Series of Ruthenium Terpyridine Water Oxidation Catalyst Chem. Eur. J. 27, 16871-16878, (2021), DOI: 10.1002/chem.202102905 Cover Image: Redox-Neutral Selenium-Catalysed Isomerisation of para-Hydroxamic Acids into para-Aminophenols Angew. Chem. 60, 13778-13782, (2021), DOI: 10.1002/anie.202100801 Cover Image: H. Chuang, M. Schupp, R. Meyrelles, B. Maryasin, N. Maulide Meyer-Schuster-type Rearrangement for the Synthesis of α-Selanyl-α,β-Unsaturated Thioesters Chem. Commun. 57, 117-120, (2021), DOI: 10.1039/D0CC07019J 25. W. Zawodny, C. J. Teskey, M. Mishevska, M. Völkl, B. Maryasin, L. González, N. Maulide Alpha-functionalisation of Ketones through Metal-Free Electrophilic Activation Angew. Chem. Int. Ed. 59, 20935-20939, (2020), DOI: 10.1002/anie.202006398 W. Zawodny, C. J. Teskey, M. Mishevska, M. Völkl, B. Maryasin, L. González, N. Maulide Unified Approach to the Chemoselective α-Functionalization of Amides with Heteroatom Nucleophiles J. Am. Chem. Soc. 141, 18437-18443, (2019), DOI: 10.1021/jacs.9b06956 23. Y. Chen, G. Coussanes, C. Souris, P. Aillard, D. Kaldre, K. Runggatscher, S. Kubicek, G. Di Mauro, B. Maryasin, N. Maulide A Domino 10-Step Total Synthesis of FR252921 and Its Analogues, Complex Macrocyclic Immunosuppressants J. Am. Chem. Soc. 141, 13772-13777, (2019), DOI: 10.1021/jacs.9b07185 22. J. Li, R. Oost, B. Maryasin, L. González, N. Maulide A Redox-Neutral Synthesis of Ketones by Coupling of Alkenes and Amides Nat. Commun. 10, 2327, (2019), DOI: 10.1038/s41467-019-10151-x Press release: On the Stability of Disubstituted Cyclobutenes - A Computational Study Eur. J. Org. Chem. 2-3, 338-341, (2019), DOI: 10.1002/ejoc.201801243 Cover Image Redox-Neutral Synthesis of Selenoesters by Oxyarylation of Selenoalkynes under Mild Conditions Org. Lett. 20, 5881-5885, (2018), DOI: 10.1021/acs.orglett.8b02544 19. B. Maryasin, P. Marquetand, N. Maulide Machine Learning for Organic Synthesis: Robots Replacing Chemists? Angew. Chem. Int. Ed. 57, 6978-6980, (2018), DOI: 10.1002/anie.201803562 18. B. Maryasin, D. Kaldre, R. Galaverna, S. Ruider, M. Drescher, H. Kählig, L. González, M. Eberlin, I. Jurberg, N. Maulide Unusual Mechanisms in Claisen Rearrangements: Ionic Fragmentation and Apparent Meta-Selective Arylation Chem. Sci. 9, 4124-4131, (2018), DOI: 10.1039/C7SC04736C 17. A. Pinto, D. Kaiser, B. Maryasin, G. di Mauro, L. González, N. Maulide Hydrative Aminoxylation of Ynamides: One Reaction, Two Mechanisms Chem. Eur. J. 24, 2515-2519, (2018), DOI: 10.1002/chem.201706063 16. G. Di Mauro, B. Maryasin, D. Kaiser, S. Shaaban, L. González, N. Maulide Mechanistic Pathways in Amide Activation: Flexible Synthesis of Oxazoles and Imidazoles Org. Lett. 19, 3815-3818, (2017), DOI: 10.1021/acs.orglett.7b01678 15. V. Tona, B. Maryasin, A. de la Torre, J. Sprachmann, L. González, N. Maulide Direct Regioselective Synthesis of Tetrazolium Salts by Activation of Secondary Amides Under Mild Conditions Org. Lett. 19, 2662-2665, (2017), DOI: 10.1021/acs.orglett.7b01004 14. J. Egli, C. Siebler, B. Maryasin, R. S. Erdmann, C. Bergande, C. Ochsenfeld, H. Wennemers pH-Responsive Aminoproline-Containing Collagen Triple Helices Chem. Eur. J. 23, 7938-7944, (2017), DOI: 10.1002/chem.201701134 13. D. Kaldre, B. Maryasin, D. Kaiser, O. Gajsek, L. González, N. Maulide An Asymmetric Redox Arylation: Chirality Transfer from Sulfur to Carbon via a Sulfonium [3,3]-Rearrangement Angew. Chem. Int. Ed. 56, 2212-2215, (2017), DOI: 10.1002/anie.201610105 D. Kaldre, B. Maryasin, D. Kaiser, O. Gajsek, L. González, N. Maulide Intermolecular 119Sn, 31P Through-Space Spin-Spin Coupling in a Solid Bivalent Tin Phosphido Complex Inorg. Chem. 55, 4669-4675, (2016), DOI: 10.1021/acs.inorgchem.6b00573 11. C. Siebler, B. Maryasin, M. Kuemin, R. S. Erdmann, C. Rigling, C. Grünenfelder, C. Ochsenfeld, H. Wennemers Importance of dipole moments and ambient polarity for the conformation of Xaa-Pro moieties - a combined experimental and theoretical study Chem. Sci. 6, 6725-6730, (2015), DOI: 10.1039/C5SC02211H 10. K.-O. Feldmann, T. Wiegand, J. Ren, H. Eckert, J. Breternitz, M. F. Groh, U. Müller, M. Ruck, B. Maryasin, C. Ochsenfeld, O. Schön, K. Karaghiosoff, J. J. Weigand [P3Se4]+: A Binary Phosphorus-Selenium Cation Chem. Eur. J. 21, 9697-9712, (2015), DOI: 10.1002/chem.201406476 9. B. Maryasin, M. Olbrich, D. Trauner, C. Ochsenfeld Calculated Nuclear Magnetic Resonance Spectra of Polytwistane and Related Hydrocarbon Nanorods J. Chem. Theory Comput. 11, 1020-1026, (2015), DOI: 10.1021/ct5011505 8. C. Lindner, Y. Liu, K. Karaghiosoff, B. Maryasin, H. Zipse The Aza-Morita-Baylis-Hillman Reaction: a Mechanistic and Kinetic Stud Chem. Eur. J. 19, 6429-6434, (2013), DOI: 10.1002/chem.201204006 7. C. Lindner, R. Tandon, B. Maryasin, E. Larionov, H. Zipse Cation affinity numbers of Lewis bases Beilstein J. Org. Chem. 8, 1406-1442, (2012), DOI: 10.3762/bjoc.8.163 6. C. Lindner, R. Tandon, Y. Liu, B. Maryasin, H. Zipse The aza-Morita-Baylis-Hillman Reaction of Electronically and Sterically Deactivated Substrates Org. Biomol. Chem. 10, 3210-3218, (2012), DOI: 10.1039/c2ob07058h 5. B. Maryasin, H. Zipse Theoretical Studies of 31P NMR Spectral Properties of Phosphanes and Related Compounds in Solution Phys. Chem. Chem. Phys. 13, 5150-5158, (2011), DOI: 10.1039/c0cp02653k 4. C. Lindner, B. Maryasin, F. Richter, H. Zipse Methyl cation affinity (MCA) values for phosphanes J. Phys. Org. Chem. 23, 1036-1042, (2010), DOI: 10.1002/poc.1726 3. Y. Wei, B. Sateesh, B. Maryasin, G. N. Sastry, H. Zipse The performance of computational techniques in locating the charge separated intermediates in organocatalytic transformations J. Comp. Chem. 30, 2617-2624, (2009), DOI: 10.1002/jcc.21271 2. L. P. Stepovik, M. V. Gulenova, I. M. Martynova, B. Maryasin, V. K. Cherkasov Titanium Tetra-tert-butoxide-tert-Butyl Hydroperoxide Oxidizing System: Physicochemical and Chemical Aspects Russ. J. General Chem. 78, 266-276, (2008), DOI: 10.1134/S1070363208020151 1. B. Maryasin, A. S. Shavyrin, J.-P. Finet, A. Yu. Fedorov Use of 2-(methoxycarbonyl)phenyllead triacetate in lactone synthesis Russ. Chem. Bull. 55, 1612-1616, (2006), DOI: 10.1007/s11172-006-0462-1 |