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  • 1.
    Martinez-Erro, Samuel
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bermejo Gómez, Antonio
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Vazquez-Romero, Ana
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Erbing, Elis
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    2,2-Diiododimedone: a mild electrophilic iodinating agent for the selective synthesis of alpha-iodoketones from allylic alcohols2017In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 53, no 71, p. 9842-9845Article in journal (Refereed)
    Abstract [en]

    2,2-Diiodo-5,5-dimethylcyclohexane-1,3-dione is reported as a new electrophilic iodinating agent that selectively iodinates electron-rich aromatics. In contrast to other common electrophilic iodinating reagents, its mild nature allows it to be used for the selective synthesis of alpha-iodinated carbonyl compounds from allylic alcohols through a 1,3-hydrogen shift/iodination process catalyzed by iridium(III) complexes.

  • 2.
    Martinez-Erro, Samuel
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    García-Vázquez, Víctor
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sanz-Marco, Amparo
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Selective Synthesis and Stereospecific Isomerization of Chiral Allylic HalidesManuscript (preprint) (Other academic)
  • 3.
    Martinez-Erro, Samuel
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sanz-Marco, Amparo
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bermejo Gómez, Antonio
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Vazquez-Romero, Ana
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ahlquist, Mårten S. G.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Base-Catalyzed Stereospecific Isomerization of Electron-Deficient Allylic Alcohols and Ethers through Ion-Pairing2016In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 138, no 40, p. 13408-13414Article in journal (Refereed)
    Abstract [en]

    A mild base-catalyzed strategy for the isomerization of allylic alcohols and allylic ethers has been developed. Experimental and computational investigations indicate that transition metal catalysts are not required when basic additives are present. As in the case of using transition metals under basic conditions, the isomerization catalyzed solely by base also follows a stereospecific pathway. The reaction is initiated by a rate-limiting deprotonation. Formation of an intimate ion pair between an allylic anion and the conjugate acid of the base results in efficient transfer of chirality. Through this mechanism, stereochemical information contained in the allylic alcohols is transferred to the ketone products. The stereospecific isomerization is also applicable for the first time to allylic ethers, yielding synthetically valuable enantioenriched (up to 97% ee) enol ethers.

  • 4.
    Molleti, Nagaraju
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martinez-Erro, Samuel
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Carretero Cerdán, Alba
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Universidad País Vasco, Spain.
    Sanz-Marco, Amparo
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Gomez-Bengoa, Enrique
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Base-Catalyzed [1,n]-Proton Shifts in Conjugated Polyenyl Alcohols and Ethers2019In: ACS Catalysis, ISSN 2155-5435, E-ISSN 2155-5435, Vol. 9, no 10, p. 9134-9139Article in journal (Refereed)
    Abstract [en]

    The isomerization of dienyl alcohols and polyenyl alkyl ethers catalyzed by TBD (1,5,7-triazabicyclo[4.4.0]dec-5-ene) under metal-free conditions is presented. Two reaction pathways have been observed. For dienyl alcohols, the reaction proceeds by a [1,3]-proton shift to give γ,δ-unsaturated ketones exclusively. On the other hand, the reaction with polyenyl alkyl ethers gives the corresponding conjugated vinyl ethers in good yields (up to 85%), with regioselectivities up to >20:1. Experimental and computational investigations suggest that the mechanism proceeds through consecutive “chain-walking” proton shifts (“base walk”) mediated by TBD.

  • 5.
    Sanz-Marco, Amparo
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martinez-Erro, Samuel
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Selective Synthesis of Unsymmetrical Aliphatic Acyloins through Oxidation of Iridium Enolates2018In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 24, no 45, p. 11564-11567Article in journal (Refereed)
    Abstract [en]

    The first method to access unsymmetrical aliphatic acyloins is presented. The method relies on a fast 1,3-hydride shift mediated by an Ir-III complex in allylic alcohols followed by oxidation with TEMPO+. The direct conversion of allylic alcohols into acyloins is achieved in a one-pot procedure. Further functionalization of the C alpha' of the alpha-amino-oxylated ketone products gives access to highly functionalized unsymmetrical aliphatic ketones, which further highlights the utility of this transformation.

  • 6.
    Sanz-Marco, Amparo
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martinez-Erro, Samuel
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Pauze, Martin
    Gómez-Bengoa, Enrique
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    An Umpolung Strategy to React Catalytic Enols with NucleophilesManuscript (preprint) (Other academic)
  • 7.
    Sanz-Marco, Amparo
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Možina, Štefan
    Martinez-Erro, Samuel
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Iskra, Jernej
    Martín‐Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of alpha-Iodoketones from Allylic Alcohols through Aerobic Oxidative Iodination2018In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 360, no 20, p. 3884-3888Article in journal (Refereed)
    Abstract [en]

    An efficient method for the synthesis of alpha-iodoketones from allylic alcohols and elemental iodine is reported. We show in this paper that the isomerization of allylic alcohols catalyzed by iridium(III) complexes can be combined with an aerobic oxidative iodination protocol, resulting in a straightforward method for the synthesis of a wide range of alpha-iodoketones as single constitutional isomers and in high yields under mild reaction conditions.

1 - 7 of 7
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