Chemistry - A European Journal

Cover image for Vol. 20 Issue 52

Redaktion: Dr.-Ing. Karl-Eugen Kurrer

Impact Factor: 5.696

ISI Journal Citation Reports © Ranking: 2013: 22/148 (Chemistry Multidisciplinary)

Online ISSN: 1521-3765

Associated Title(s): Angewandte Chemie International Edition, Chemistry – An Asian Journal, ChemistryOpen, ChemBioChem, ChemCatChem, ChemElectroChem, ChemMedChem, ChemPhysChem, ChemPlusChem, ChemSusChem, European Journal of Inorganic Chemistry, European Journal of Organic Chemistry

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October 08, 2014

Prize-winning chemistry!

Prize-winning chemistry!

The Nobel Prize in Chemistry 2014 has been awarded jointly to Eric Betzig, Howard Hughes Medical Institute, Ashburn, VA, USA, Stefan W. Hell, Max Planck Institute for Biophysical Chemistry, Göttingen, and German Cancer Research Center, Heidelberg, Germany, and William E. Moerner, Stanford University, CA, USA, "for the development of super-resolved fluorescence microscopy".

Work from Stefan Hell and his group on masked rhodamine dyes and their applications in light microscopy applications was recently highlighted on the front cover of Chemistry—A European Journal.

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Recently Published Articles

  1. Total Synthesis and Structure Elucidation of JBIR-39: A Linear Hexapeptide Possessing Piperazic Acid and γ-Hydroxypiperazic Acid Residues

    Dr. Masahito Yoshida, Naoki Sekioka, Dr. Miho Izumikawa, Dr. Ikuko Kozone, Dr. Motoki Takagi, Dr. Kazuo Shin-ya and Prof. Dr. Takayuki Doi

    Article first published online: 18 DEC 2014 | DOI: 10.1002/chem.201406020

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    Structure solved! The total synthesis and structure elucidation of linear peptide JBIR-39 (1 b) containing an unprecedented four nonproteinogenic piperazic acid (Piz) residues, was achieved (see scheme). The approach involved efficient Sc(OTf)3-catalyzed direct acylation of Piz(γ-OTBS) derivative with piperazic acid chloride, leading to the Piz-Piz(γ-OTBS) dipeptide in high yield without epimerization.

  2. Probing o-Diphenylphosphanyl Benzoate (o-DPPB)-Directed C[BOND]C Bond Formation: Total Synthesis of Dictyostatin

    Sebastian Wünsch and Prof. Dr. Bernhard Breit

    Article first published online: 18 DEC 2014 | DOI: 10.1002/chem.201406252

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    Directed catalysis: The antitumor agent dictyostatin was synthesized by using the catalyst-directing o-DPPB group for the construction of various propionate motifs. A propionate–deoxypropionate entity was stereospecifically generated through an o-DPPB-directed, copper-catalyzed allylic substitution. An anti-propionate–olefin moiety was constructed in a regio- and stereoselective manner by an o-DPPB-directed, rhodium-catalyzed hydroformylation (see scheme).

  3. Aminocatalytic Cross-Coupling Approach via Iminium Ions to Different C[BOND]C Bonds

    Nagaraju Mupparapu , Narsaiah Battini , Satyanarayana Battula , Shahnawaz Khan , Dr. Ram A. Vishwakarma  and Dr. Qazi Naveed Ahmed 

    Article first published online: 18 DEC 2014 | DOI: 10.1002/chem.201405477

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    New iminium-ion reactivity mode: The reactivity of iminium ions containing an α C[DOUBLE BOND]O group, generated in situ by reaction of 2-oxoaldehydes with secondary amines, was developed and utilized to generate different cross-coupling products through formation of C[BOND]C and N[BOND]C bonds (see scheme). These processes proceed due to the unique ability of a three-component intermediate to undergo self-deamination and oxidation by air and, moreover, furnished the mildest possible approach to α-ketoamides.

  4. Simple Access to Highly Functional Bicyclic γ- and δ-Lactams: Origins of Chirality Transfer to Contiguous Tertiary/Quaternary Stereocenters Assessed by DFT

    Ronan Le Goff, Prof. Arnaud Martel, Dr. Morgane Sanselme, Dr. Ata Martin Lawson, Prof. Adam Daïch and Dr. Sébastien Comesse

    Article first published online: 18 DEC 2014 | DOI: 10.1002/chem.201405094

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    Double chirality transfer! Access to bicyclic γ- and δ-lactams by an acid-free domino reaction is described (see scheme). This process allows the synthesis of highly functionalized oxazolo-pyrrolidinones and -piperidinones in good yield and selectivity. Starting from (R)-phenylglycinol gives the desired bicyclic lactam with double chirality transfer, which allows the formation of two contiguous and fully controlled stereocenters. This has been assessed by DFT calculations.

  5. Solvent-Free One-Step Photochemical Hydroxylation of Benzene Derivatives by the Singlet Excited State of 2,3-Dichloro-5,6-dicyano-p-benzoquinone Acting as a Super Oxidant

    Prof. Dr. Kei Ohkubo, Kensaku Hirose and Prof. Dr. Shunichi Fukuzumi

    Article first published online: 18 DEC 2014 | DOI: 10.1002/chem.201404810

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    Super photooxidant: Photoinduced hydroxylation of neat deaerated benzene derivatives to the corresponding phenols occurred under visible-light irradiation of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ; see figure), which acts as a super photooxidant in the presence of water. The reactions are initiated by electron-transfer oxidation of benzene derivatives with the singlet and triplet excited states of DDQ to form the corresponding radical cations and DDQ..