Articles producció científicaQuímica Física i Inorgànica

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

  • Datos identificativos

    Identificador:  imarina:9242238
    Handle: https://hdl.handle.net/20.500.11797/imarina9242238
    Autores:  Wahlers, Jessica; Margalef, Jessica; Hansen, Eric; Bayesteh, Armita; Helquist, Paul; Dieguez, Montserrat; Pamies, Oscar; Wiest, Olaf; Norrby, Per-Ola
    Resumen:
    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).

  • Otros:

    Enlace a la fuente original: https://www.nature.com/articles/s41467-021-27065-2
    Referencia de l'ítem segons les normes 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
    Referencia al articulo segun fuente origial: Nature Communications. 12 (1): 6719-
    DOI del artículo: 10.1038/s41467-021-27065-2
    Año de publicación de la revista: 2021
    Entidad: Universitat Rovira i Virgili
    Versión del articulo depositado: info:eu-repo/semantics/publishedVersion
    Fecha de alta del registro: 2025-02-24
    Autor/es de la URV: Diéguez Fernández, Montserrat / Margalef Pallarès, Jèssica / Pamies Ollé, Oscar
    Departamento: Química Física i Inorgànica
    URL Documento de licencia: https://repositori.urv.cat/ca/proteccio-de-dades/
    Tipo de publicación: Journal Publications
    Autor según el artículo: Wahlers, Jessica; Margalef, Jessica; Hansen, Eric; Bayesteh, Armita; Helquist, Paul; Dieguez, Montserrat; Pamies, Oscar; Wiest, Olaf; Norrby, Per-Ola
    Acceso a la licencia de uso: https://creativecommons.org/licenses/by/3.0/es/
    Áreas temáticas: 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
    Direcció de correo del autor: oscar.pamies@urv.cat, montserrat.dieguez@urv.cat

  • Palabras clave:

    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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