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  1. Article ; Online: Tungsten's tandem transformation.

    Jenny, Sarah E / Dobereiner, Graham E

    Nature chemistry

    2022  Volume 14, Issue 6, Page(s) 594–595

    MeSH term(s) Tungsten
    Chemical Substances Tungsten (V9306CXO6G)
    Language English
    Publishing date 2022-06-02
    Publishing country England
    Document type Journal Article ; Comment
    ZDB-ID 2464596-5
    ISSN 1755-4349 ; 1755-4330
    ISSN (online) 1755-4349
    ISSN 1755-4330
    DOI 10.1038/s41557-022-00953-w
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article ; Online: Beyond Bioisosteres: Divergent Synthesis of Azabicyclohexanes and Cyclobutenyl Amines from Bicyclobutanes.

    Dhake, Kushal / Woelk, Kyla J / Becica, Joseph / Un, Andy / Jenny, Sarah E / Leitch, David C

    Angewandte Chemie (International ed. in English)

    2022  Volume 61, Issue 27, Page(s) e202204719

    Abstract: The development of two divergent and complementary Lewis acid catalyzed additions of bicyclobutanes to imines is described. Microscale high-throughput experimentation was integral to the discovery and optimization of both reactions. N-arylimines undergo ... ...

    Abstract The development of two divergent and complementary Lewis acid catalyzed additions of bicyclobutanes to imines is described. Microscale high-throughput experimentation was integral to the discovery and optimization of both reactions. N-arylimines undergo formal (3+2) cycloaddition with bicyclobutanes to yield azabicyclo[2.1.1]hexanes in a single step; in contrast, N-alkylimines undergo an addition/elimination sequence to generate cyclobutenyl methanamine products with high diastereoselectivity. These new products contain a variety of synthetic handles for further elaboration, including many functional groups relevant to pharmaceutical synthesis. The divergent reactivity observed is attributed to differences in basicity and nucleophilicity of the nitrogen atom in a common carbocation intermediate, leading to either nucleophilic attack (N-aryl) or E1 elimination (N-alkyl).
    MeSH term(s) Amines ; Butanes/chemistry ; Cycloaddition Reaction ; Imines ; Lewis Acids ; Molecular Structure
    Chemical Substances Amines ; Butanes ; Imines ; Lewis Acids
    Language English
    Publishing date 2022-05-03
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.202204719
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article ; Online: Chiral, air stable, and reliable Pd(0) precatalysts applicable to asymmetric allylic alkylation chemistry.

    Huang, Jingjun / Keenan, Thomas / Richard, François / Lu, Jingru / Jenny, Sarah E / Jean, Alexandre / Arseniyadis, Stellios / Leitch, David C

    Nature communications

    2023  Volume 14, Issue 1, Page(s) 8058

    Abstract: Stereoselective carbon-carbon bond formation via palladium-catalyzed asymmetric allylic alkylation is a crucial strategy to access chiral natural products and active pharmaceutical ingredients. However, catalysts based on the privileged Trost and Pfaltz- ... ...

    Abstract Stereoselective carbon-carbon bond formation via palladium-catalyzed asymmetric allylic alkylation is a crucial strategy to access chiral natural products and active pharmaceutical ingredients. However, catalysts based on the privileged Trost and Pfaltz-Helmchen-Williams PHOX ligands often require high loadings, specific preactivation protocols, and excess chiral ligand. This makes these reactions uneconomical, often unreproducible, and thus unsustainable. Here we report several chiral single-component Pd(0) precatalysts that are active and practically-applicable in a variety of asymmetric allylic alkylation reactions. Despite the decades-long history and widespread use of Trost-type ligands, the precatalysts in this work are the only reported examples of stable, isolable Pd(0) complexes with these ligands. Evaluating these precatalysts across nine asymmetric allylic alkylation reactions reveals high reactivity and selectivity at low Pd loading. Importantly, we also report an unprecedented Pd-catalyzed enantioselective allylation of a hydantoin, achieved on gram scale in high yield and enantioselectivity with only 0.2 mol% catalyst.
    Language English
    Publishing date 2023-12-05
    Publishing country England
    Document type Journal Article
    ZDB-ID 2553671-0
    ISSN 2041-1723 ; 2041-1723
    ISSN (online) 2041-1723
    ISSN 2041-1723
    DOI 10.1038/s41467-023-43512-8
    Database MEDical Literature Analysis and Retrieval System OnLINE

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