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  • 1.
    Alam, Rauful
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Diner, Colin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Jonker, Sybrand
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Eriksson, Lars
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Catalytic Asymmetric Allylboration of Indoles and Dihydroisoquinolines with Allylboronic Acids: Stereodivergent Synthesis of up to Three Contiguous Stereocenters2016In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 55, no 46, p. 14417-14421Article in journal (Refereed)
    Abstract [en]

    The catalytic asymmetric allylboration of cyclic imines with gamma,gamma-disubstituted allylboronic acids provides products with adjacent stereocenters in high yield and stereoselectivity. Various electrophiles, including 3,4-dihydroisoquinolines and indoles, were prenylated in a fully stereodivergent fashion by switching the E/Z geometry of the allylboronate and/or the enantiomer of the BINOL catalyst. 3-Methylindole provided products with three adjacent stereocenters with high stereoselectivity in one synthetic operation.

  • 2.
    Jonker, Sybrand J. T.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Diner, Colin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Schulz, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Iwamoto, Hiroaki
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Eriksson, Lars
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Catalytic asymmetric propargyl- and allylboration of hydrazonoesters: a metal-free approach to sterically encumbered chiral alpha-amino acid derivatives2018In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 54, no 91, p. 12852-12855Article in journal (Refereed)
    Abstract [en]

    A new asymmetric catalytic propargyl- and allylboration of hydrazonoesters is reported. The reactions utilize allenyl- and allylboronic acids in the presence of the inexpensive parent BINOL catalyst. The reactions can be performed under mild conditions (0 degrees C) without any metal catalyst or other additives affording sterically encumbered chiral -amino acids. This is the first metal-free method for the asymmetric propargyl- and allylboration of hydrazonoesters.

  • 3.
    Zhao, Jian
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Jonker, Sybrand J. T.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Meyer, Denise N.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Schulz, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Tran, C. Duc
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Eriksson, Lars
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Copper-catalyzed synthesis of allenylboronic acids. Access to sterically encumbered homopropargylic alcohols and amines by propargylboration2018In: Chemical Science, ISSN 2041-6520, E-ISSN 2041-6539, Vol. 9, no 13, p. 3305-3312Article in journal (Refereed)
    Abstract [en]

    Tri- and tetrasubstituted allenylboronic acids were prepared via a new versatile copper-catalyzed methodology. The densely functionalized allenylboronic acids readily undergo propargylboration reactions with ketones and imines without any additives. Catalytic asymmetric propargylborylation of ketones is demonstrated with high stereoselectivity allowing for the synthesis of highly enantioenriched tertiary homopropargyl alcohols. The reaction is suitable for kinetic resolution of racemic allenylboronic acids affording alkynes with adjacent quaternary stereocenters.

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