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    Switchable Diastereoselectivity in the Fluoride Promoted Vinylogous Mukaiyama-Michael Reaction of 2-Trimethylsilyloxyfuran Catalyzed by Crown Ethers

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    Type
    Article
    Authors
    Della Sala, Giorgio
    Sicignano, Marina
    Schettini, Rosaria
    De Riccardis, Francesco
    Cavallo, Luigi cc
    Minenkov, Yury cc
    Batisse, Chloé
    Hanquet, Gilles
    Leroux, Frederic
    IZZO, Irene
    KAUST Department
    Chemical Science Program
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2017-06-13
    Online Publication Date
    2017-06-13
    Print Publication Date
    2017-07-07
    Permanent link to this record
    http://hdl.handle.net/10754/624886
    
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    Abstract
    The fluoride promoted vinylogous Mukaiyama-Michael reaction (VMMR) of 2-trimethylsilyloxyfuran with diverse α,β-unsaturated ketones is described. The TBAF catalyzed VMMR afforded high anti-diastereoselectivity irrespective of the solvents used. The KF/crown ethers catalytic systems proved to be highly efficient in terms of yields and resulted in a highly diastereoselective unprecedented solvent/catalyst switchable reaction. Anti-adducts were obtained as single diastereomers or with excellent diastereoselectivities when benzo-15-crown-5 in CH2Cl2 was employed. On the other hand, high syn-diastereoselectivities (from 76:24 to 96:4) were achieved by employing dicyclohexane-18-crown-6 in toluene. Based on DFT calculations, the catalysts/solvents-dependent switchable diastereoselectivities are proposed to be the result of loose or tight cation-dienolate ion pairs.
    Citation
    Della Sala G, Sicignano M, Schettini R, De Riccardis F, Cavallo L, et al. (2017) Switchable Diastereoselectivity in the Fluoride Promoted Vinylogous Mukaiyama-Michael Reaction of 2-Trimethylsilyloxyfuran Catalyzed by Crown Ethers. The Journal of Organic Chemistry. Available: http://dx.doi.org/10.1021/acs.joc.7b00743.
    Sponsors
    Financial support from the University of Salerno (FARB) and Regione Campania under POR Campania FESR 2007-2013 – O.O. 2.1 (Farma-BioNet). We thank Dr. Patrizia Iannece for HRMS. Gilles Hanquet and Frédéric Leroux thank the CNRS (Centre National de la Recherche Scientifique, France). Chloé Batisse is very grateful to the IcFRC (International Center for Frontier Research in Chemistry), grant Cyclo-CF2-ASYM. Luigi Cavallo thanks the King Abdullah University of Science and technology for supporting this work. Computing resources used within this project have been provided by the KAUST Supercomputing Laboratory and by CRESCO/ENEAGRID High Performance Computing infrastructure and its staff.
    Publisher
    American Chemical Society (ACS)
    Journal
    The Journal of Organic Chemistry
    DOI
    10.1021/acs.joc.7b00743
    PubMed ID
    28561585
    Additional Links
    http://pubs.acs.org/doi/abs/10.1021/acs.joc.7b00743
    ae974a485f413a2113503eed53cd6c53
    10.1021/acs.joc.7b00743
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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