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  • Primary trifluoroborate-iminiums enable facile access to chiral α-aminoboronic acids via ru-catalyzed asymmetric hydrogenation and simple hydrolysis of trifluoroborate moiety [Elektronski vir]
    Šterman, Andrej, farmacevt ; Sosič, Izidor ; Časar, Zdenko
    This work describes the first preparation and application of primary trifluoroborate-iminiums (pTIMs) as new, easily accessible and valuable class of organoboron derivatives. An array of structurally ... diverse pTIMs was prepared from potassium acyltrifluoroborates in excellent yields. Highly efficient and enantioselective [(R,R)-TethTsDpen-RuCl] complex-catalyzed hydrogenation of pTIMS provided direct access to the chiral primary trifluoroborate-ammoniums (pTAMs). Moreover, facile synthesis of a series of structurally diverse chiral α-aminoboronic acids from chiral pTAMs was accomplished through novel, operationally simple and efficient conversion using hexamethyldisiloxane/aqueous HCl. Using no chromatography at any point, this work allowed easy access to chiral α-aminoboronic acids, as exemplified by the synthesis of optically pure anti-cancer drugs bortezomib and ixazomib.
    Vir: Chemical science [Elektronski vir]. - ISSN 2041-6539 (Vol. 13, issue. 10, 2022, str. 2946-2953)
    Vrsta gradiva - e-članek ; neleposlovje za odrasle
    Leto - 2022
    Jezik - angleški
    COBISS.SI-ID - 95169795

    Povezava(-e):

    https://pubs.rsc.org/en/content/articlelanding/2022/sc/d1sc07065g
    DOI

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