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  1. Article ; Online: Enolate addition to bicyclobutanes enables expedient access to 2-oxo-bicyclohexane scaffolds.

    Woelk, Kyla J / Dhake, Kushal / Schley, Nathan D / Leitch, David C

    Chemical communications (Cambridge, England)

    2023  Volume 59, Issue 93, Page(s) 13847–13850

    Abstract: We report the synthesis of 2-oxo-bicyclo[2.1.1]hexanes (2-oxo-BCHs) from bicyclobutanes (BCBs) and readily available enolate precursors. Glycine-derived enolates directly give protected 2-oxo-3-amino-BCH derivatives that can be further functionalized. ... ...

    Abstract We report the synthesis of 2-oxo-bicyclo[2.1.1]hexanes (2-oxo-BCHs) from bicyclobutanes (BCBs) and readily available enolate precursors. Glycine-derived enolates directly give protected 2-oxo-3-amino-BCH derivatives that can be further functionalized. Arylacetate derivatives are also suitable enolate precursors, giving 2-oxo-3-aryl-BCH scaffolds from readily available starting materials.
    Language English
    Publishing date 2023-11-21
    Publishing country England
    Document type Journal Article
    ZDB-ID 1472881-3
    ISSN 1364-548X ; 1359-7345 ; 0009-241X
    ISSN (online) 1364-548X
    ISSN 1359-7345 ; 0009-241X
    DOI 10.1039/d3cc04234k
    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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