Articles producció científicaQuímica Física i Inorgànica

Proofreading experimentally assigned stereochemistry through Q2MM predictions in Pd-catalyzed allylic aminations

  • Identification data

    Identifier:  imarina:9242238
    Handle: https://hdl.handle.net/20.500.11797/imarina9242238
    Authors:  Wahlers, Jessica; Margalef, Jessica; Hansen, Eric; Bayesteh, Armita; Helquist, Paul; Dieguez, Montserrat; Pamies, Oscar; Wiest, Olaf; Norrby, Per-Ola
    Abstract:
    The palladium-catalyzed enantioselective allylic substitution by carbon or nitrogen nucleophiles is a key transformation that is particularly useful for the synthesis of bioactive compounds. Unfortunately, the selection of a suitable ligand/substrate combination often requires significant screening effort. Here, we show that a transition state force field (TSFF) derived by the quantum-guided molecular mechanics (Q2MM) method can be used to rapidly screen ligand/substrate combinations. Testing of this method on 77 literature reactions revealed several cases where the computationally predicted major enantiomer differed from the one reported. Interestingly, experimental follow-up led to a reassignment of the experimentally observed configuration. This result demonstrates the power of mechanistically based methods to predict and, where necessary, correct the stereochemical outcome. © 2021, The Author(s).

  • Others:

    Link to the original source: https://www.nature.com/articles/s41467-021-27065-2
    APA: Wahlers, Jessica; Margalef, Jessica; Hansen, Eric; Bayesteh, Armita; Helquist, Paul; Dieguez, Montserrat; Pamies, Oscar; Wiest, Olaf; Norrby, Per-Ola (2021). Proofreading experimentally assigned stereochemistry through Q2MM predictions in Pd-catalyzed allylic aminations. Nature Communications, 12(1), 6719-. DOI: 10.1038/s41467-021-27065-2
    Paper original source: Nature Communications. 12 (1): 6719-
    Article's DOI: 10.1038/s41467-021-27065-2
    Journal publication year: 2021
    Entity: Universitat Rovira i Virgili
    Paper version: info:eu-repo/semantics/publishedVersion
    Record's date: 2025-02-24
    URV's Author/s: Diéguez Fernández, Montserrat / Margalef Pallarès, Jèssica / Pamies Ollé, Oscar
    Department: Química Física i Inorgànica
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Publication Type: Journal Publications
    Author, as appears in the article.: Wahlers, Jessica; Margalef, Jessica; Hansen, Eric; Bayesteh, Armita; Helquist, Paul; Dieguez, Montserrat; Pamies, Oscar; Wiest, Olaf; Norrby, Per-Ola
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    Thematic Areas: Zootecnia / recursos pesqueiros, Saúde coletiva, Química, Psicología, Planejamento urbano e regional / demografia, Physics and astronomy (miscellaneous), Physics and astronomy (all), Odontología, Nutrição, Multidisciplinary sciences, Multidisciplinary, Medicina veterinaria, Medicina iii, Medicina ii, Medicina i, Materiais, Matemática / probabilidade e estatística, Interdisciplinar, Geociências, General physics and astronomy, General medicine, General chemistry, General biochemistry,genetics and molecular biology, Farmacia, Engenharias iv, Educação física, Ciências biológicas iii, Ciências biológicas ii, Ciências biológicas i, Ciências ambientais, Ciências agrárias i, Ciência da computação, Chemistry (miscellaneous), Chemistry (all), Biotecnología, Biodiversidade, Biochemistry, genetics and molecular biology (miscellaneous), Biochemistry, genetics and molecular biology (all), Astronomia / física, Antropologia / arqueologia
    Author's mail: oscar.pamies@urv.cat, montserrat.dieguez@urv.cat

  • Keywords:

    Stereochemistry
    Prediction
    Palladium
    Molecular mechanics
    Molecular analysis
    Mechanics
    Ligand
    Follow up
    Experimental study
    Enantiomer
    Drug synthesis
    Conformational transition
    Chemistry
    Catalysis
    Article
    Amination
    Biochemistry
    Genetics and Molecular Biology (Miscellaneous)
    Chemistry (Miscellaneous)
    Multidisciplinary Sciences
    Physics and Astronomy (Miscellaneous)
    Zootecnia / recursos pesqueiros
    Saúde coletiva
    Química
    Psicología
    Planejamento urbano e regional / demografia
    Physics and astronomy (all)
    Odontología
    Nutrição
    Multidisciplinary
    Medicina veterinaria
    Medicina iii
    Medicina ii
    Medicina i
    Materiais
    Matemática / probabilidade e estatística
    Interdisciplinar
    Geociências
    General physics and astronomy
    General medicine
    General chemistry
    General biochemistry
    genetics and molecular biology
    Farmacia
    Engenharias iv
    Educação física
    Ciências biológicas iii
    Ciências biológicas ii
    Ciências biológicas i
    Ciências ambientais
    Ciências agrárias i
    Ciência da computação
    Chemistry (all)
    Biotecnología
    Biodiversidade
    genetics and molecular biology (all)
    Astronomia / física
    Antropologia / arqueologia

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