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  • 1.
    Deng, Youqian
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bartholomeyzik, Teresa
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Persson, Andreas K. A.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sun, Junliang
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Palladium-Catalyzed Oxidative Arylating Carbocyclization of Allenynes2012In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 51, no 11, p. 2703-2707Article in journal (Refereed)
  • 2.
    Jiang, Tuo
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Persson, Andreas K. A.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Palladium-Catalyzed Oxidative Carbocyclization/Arylation of Enallenes2011In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 13, no 21, p. 5838-5841Article in journal (Refereed)
    Abstract [en]

    A stereoselective palladium-catalyzed oxidative carbocyclization/arylation of enallenes is described. The reaction shows wide tolerance toward highly functionalized arylboronic acids and results In a cis addition of two carbon moieties to an olefin in good to excellent yields.

  • 3.
    Joosten, Antoine
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Persson, Andreas K. A.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Millet, Renaud
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Johnson, Magnus T.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Palladium(II)-Catalyzed Oxidative Cyclization of Allylic Tosylcarbamates: Scope, Derivatization, and Mechanistic Aspects2012In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 18, no 47, p. 15151-15157Article, review/survey (Refereed)
    Abstract [en]

    A highly selective oxidative palladium(II)-catalyzed (Wacker-type) cyclization of readily available allylic tosylcarbamates is reported. This operationally simple catalytic reaction furnishes tosyl-protected vinyl-oxazolidinones, common precursors to syn-1,2-amino alcohols, in high yield and excellent diasteroselectivity (>20:1). It is demonstrated that both stoichiometric amounts of benzoquinone (BQ) as well as aerobic reoxidation (molecular oxygen) is suitable for this transformation. The title reaction is shown to proceed through overall trans-amidopalladation of the olefin followed by beta-hydride elimination. This process is scalable and the products are suitable for a range of subsequent transformations such as: kinetic resolution (KR) and oxidative Heck-, Wacker-, and metathesis reactions.

  • 4.
    Persson, Andreas
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Palladium(II)-catalyzed carbocyclizations. Moving from enallenes to aza-enallenes.2010Licentiate thesis, comprehensive summary (Other academic)
  • 5.
    Persson, Andreas K. A.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Jiang, Tuo
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Johnson, Magnus T.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Palladium-Catalyzed Oxidative Borylative Carbocyclization of Enallenes2011In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 50, no 27, p. 6155-6159Article in journal (Refereed)
    Abstract [en]

    An efficient oxidative carbocyclization/borylation of enallenes uses Pd(OAc)2 as the catalyst, B2pin2 as the boron-transfer reagent, and 1,4-benzoquinone (BQ) as the oxidant (see scheme). The reaction seems to take place through activation of the allene by a PdII complex to give an alkenyl–PdII intermediate followed by carbopalladation of the olefin and subsequent cleavage of the intermediate palladium–carbon bond by the boron reagent.

  • 6.
    Persson, Andreas K. Å.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Palladium(II)-Catalyzed Oxidative Cyclization Strategies: Selective Formation of New C-C and C-N Bonds2012Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    The main focus of this thesis has been directed towards preparation and oxidative carbocyclization of en-, dien- and aza-enallenes.

    In the first part of this thesis, a stereoselective oxidative carbocyclization of dienallenes was realized. By employing cheap and readily available palladium trifluoroacetate we were able to efficiently cyclize a variety of dienallenes into hydroxylated carbocycles in high yield and high selectivity. This oxidative process was compatible with two different reoxidation protocols: one relying on p-benzoquinone (BQ) as the oxidant and the other employing molecular oxygen as the oxidant.

    In the second part of the thesis the carbocyclization methodology was extended to include carbocyclization of aza-enallenes. This was achieved in two distinct steps. First, a copper-catalyzed coupling of allylic sulfonamides with bromoallenes was developed, giving access to the corresponding aza-enallenes. Subjecting these substrates to catalytic amounts of palladium acetate, along with BQ as the oxidant, rendered N-heterocycles in good yield. The reactivity of these N-heterocycles towards activated dienophiles was later exploited in a tandem (aerobic) oxidative carbocyclization/Diels-Alder reaction.

    The third topic involves efficient oxidative arylative/borylative carbocyclization of enallenes. These reactions, catalyzed by palladium acetate, relies on transmetallation of a (σ-alkyl)palladium(II) intermediate with diboranes or arylboronic acids. With this novel methodology we were able to obtain an array of arylated or borylated carbocycles, as single diastereomers, in high yield.

    Finally, we developed a palladium(II)-catalyzed cyclization of allylic carbamates. This mild, operationally simple, and scalable catalytic reaction opens up access to an array of oxazolidinones in high yield and excellent diastereoselectivity.

  • 7.
    Persson, Andreas K. Å.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Palladium(II)-catalyzed oxidative carbocyclization of aza-enallenes2010In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 49, no 27, p. 4624-4627Article in journal (Refereed)
    Abstract [en]

    Live and let diene: A palladium(II)-catalyzed oxidative carbocyclization reaction of aza-enallenes provides access to potentially valuable heterocyclic dienes. In the presence of a dieneophile during the carbocyclization step, the products can react further in a one-pot cyclization/Diels–Alder sequence to give polycyclic products. BQ=para-benzoquinone

  • 8.
    Persson, Andreas K. Å.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Johnston, Eric V.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Copper-catalyzed N-allenylation of allylic sulfonamides2009In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 11, no 17, p. 3814-3817Article in journal (Refereed)
    Abstract [en]

    Allylic allenic amides have been synthesized via a copper-catalyzed cross-coupling between allylic sulfonamides and bromoallenes in moderate to good yields. Copper(I) thiophene-2-carboxylate (CuTC) was used a source of copper with DMEDA as the ligand. The allenylated products obtained are potential substrates for palladium-catalyzed carbocyclizations.

  • 9.
    Piera, Julio
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Persson, Andreas
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Caldentey, Xisco
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Water as nucleophile in palladium-catalyzed oxidative carbohydroxylation of allene-substituted conjugated dienes2007In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 129, no 46, p. 14120-14121Article in journal (Refereed)
    Abstract [en]

    An efficient palladium(II)-catalyzed oxidative carbohydroxylation of allene-substituted conjugated dienes in aqueous media has been developed. The reaction is conducted employing p-benzoquinone as the stoichiometric reoxidant for the palladium or under aerobic conditions with essentially the same outcome. It is worth mentioning that this is the first example of a palladium(II)-catalyzed oxidation where a carbon−carbon bond is formed in water and also one of the few cases of nucleophilic attack by water on a (π-allyl)palladium complex.

  • 10.
    Thalén, Lisa K.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sumic, Anna
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bogár, Krisztián
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Norinder, Jacob
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Persson, Andreas K. Å.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Enantioselective synthesis of α-methyl carboxylic acids from readily available starting materials via chemoenzymatic dynamic kinetic resolution2010In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 75, no 20, p. 6842-6847Article in journal (Refereed)
    Abstract [en]

    An enantioselective method for the synthesis of α-methyl carboxylic acids starting from trans-cinnamaldehyde, a readily available and inexpensive compound, has been developed. Allylic alcohol 1 was obtained via a standard Grignard addition to trans-cinnamaldehyde. Dynamic kinetic resolution was applied to allylic alcohol 1 utilizing a ruthenium catalyst and either an (R)-selective lipase or an (S)-selective protease to provide the corresponding allylic esters in high yield and high ee. A copper-catalyzed allylic substitution was then applied to provide the corresponding alkenes with inversion of stereochemistry. Subsequent C−C double bond cleavage afforded pharmaceutically important α-methyl substituted carboxylic acids in high ee and overall yields of up to 76%.

1 - 10 of 10
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