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    Catalytic Asymmetric Piancatelli Rearrangement: Brønsted Acid Catalyzed 4π Electrocyclization for the Synthesis of Multisubstituted Cyclopentenones

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    Type
    Article
    Authors
    Cai, Yunfei
    Tang, Yurong
    Atodiresei, Iuliana
    Rueping, Magnus cc
    KAUST Department
    Chemical Science Program
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2016-10-10
    Online Publication Date
    2016-10-10
    Print Publication Date
    2016-11-02
    Permanent link to this record
    http://hdl.handle.net/10754/623161
    
    Metadata
    Show full item record
    Abstract
    The first catalytic asymmetric Piancatelli reaction is reported. Catalyzed by a chiral Brønsted acid, the rearrangement of a wide range of furylcarbinols with a series of aniline derivatives provides valuable aminocyclopentenones in high yields as well as excellent enantioselectivities and diastereoselectivities. The high value of the aza-Piancatelli rearrangement was demonstrated by the synthesis of a cyclopentane-based hNK1 antagonist analogue.
    Citation
    Cai Y, Tang Y, Atodiresei I, Rueping M (2016) Catalytic Asymmetric Piancatelli Rearrangement: Brønsted Acid Catalyzed 4π Electrocyclization for the Synthesis of Multisubstituted Cyclopentenones. Angewandte Chemie International Edition 55: 14126–14130. Available: http://dx.doi.org/10.1002/anie.201608023.
    Sponsors
    Y.C. thanks the Alexander von Humboldt foundation for afellowship. Financial support by the DFG is gratefully acknowledged.
    Publisher
    Wiley
    Journal
    Angewandte Chemie
    DOI
    10.1002/anie.201608023
    10.1002/ange.201608023
    Additional Links
    http://onlinelibrary.wiley.com/doi/10.1002/anie.201608023/abstract
    ae974a485f413a2113503eed53cd6c53
    10.1002/anie.201608023
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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