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Publication - Professor Carmen Galan

    Substrate-Controlled Direct α-Stereoselective Synthesis of Deoxyglycosides from Glycals Using B(C 6 F 5 ) 3 as Catalyst

    Citation

    Sau, A, Palo-Nieto, C & Galan, MC, 2019, ‘Substrate-Controlled Direct α-Stereoselective Synthesis of Deoxyglycosides from Glycals Using B(C 6 F 5 ) 3 as Catalyst’. Journal of Organic Chemistry, vol 84., pp. 2415-2424

    Abstract


    B(C
    6
    F
    5
    )
    3
    enables the metal-free unprecedented substrate-controlled direct α-stereoselective synthesis of deoxyglycosides from glycals. 2,3-Unsaturated α-O-glycoside products are obtained with deactivated glycals at 75 °C in the presence of the catalyst, while 2-deoxyglycosides are formed using activated glycals that bear no leaving group at C-3 at lower temperatures. The reaction proceeds in good to excellent yields via concomitant borane activation of glycal donor and nucleophile acceptor. The method is exemplified with the synthesis of a series of rare and biologically relevant glycoside analogues.

    Full details in the University publications repository