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    Unprecedented Diastereoselective Arylogous Michael Addition of Unactivated Phthalides

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    Type
    Article
    Authors
    Sicignano, Marina
    Schettini, Rosaria
    Sica, Luisa
    Pierri, Giovanni
    De Riccardis, Francesco
    IZZO, Irene
    Maity, Bholanath cc
    Minenkov, Yury
    Cavallo, Luigi cc
    Della Sala, Giorgio
    KAUST Department
    Chemical Science
    Chemical Science Program
    KAUST Catalysis Center
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2019-04-08
    Online Publication Date
    2019-04-08
    Print Publication Date
    2019-05-23
    Embargo End Date
    2020-04-08
    Permanent link to this record
    http://hdl.handle.net/10754/656080
    
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    Abstract
    The first highly enantioselective arylogous Michael reaction (AMR) of 3-unsubstituted phthalides has been described. This phase-transfer methodology, which uses catalytic amounts of KOH/18-crown-6 catalyst in mesitylene in the presence of N,O-bis(trimethylsilyl)acetamide (BSA), gives access to a broad range of 3-monosubstituted phthalides with high levels of syn diastereoselectivity and good yields, starting from 3-unsubstituted derivatives and diverse α,β-unsaturated carbonyl compounds. The reaction also applies to unactivated 3-alkyl phthalides to afford 3,3-dialkyl derivatives. A plausible mechanism has been suggested. DFT analysis of possible transition states gives a rationale of the high syn diastereoselectivity observed and its correlation with the solvent's dielectric constant.
    Citation
    Sicignano, M., Schettini, R., Sica, L., Pierri, G., De Riccardis, F., Izzo, I., … Della Sala, G. (2019). Unprecedented Diastereoselective Arylogous Michael Addition of Unactivated Phthalides. Chemistry – A European Journal, 25(29), 7131–7141. doi:10.1002/chem.201900168
    Sponsors
    Financial support was provided from the University of Salerno (FARB). The computing resources used within this project have been provided by CRESCO/ENEAGRID High Performance Computing infrastructure and its staff. We thank Dr Patrizia Iannece for HR-ESI-MS
    Publisher
    Wiley
    Journal
    Chemistry – A European Journal
    DOI
    10.1002/chem.201900168
    Additional Links
    https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201900168
    Relations
    Is Supplemented By:
    • [Dataset]
      . DOI: 10.5517/ccdc.csd.cc20xzkh HANDLE: 10754/664724
    Is Supplemented By:
    • [Dataset]
      . DOI: 10.5517/ccdc.csd.cc20xzmk HANDLE: 10754/664725
    Is Supplemented By:
    • [Dataset]
      . DOI: 10.5517/ccdc.csd.cc20xzlj HANDLE: 10754/664726
    ae974a485f413a2113503eed53cd6c53
    10.1002/chem.201900168
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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