Journal: European Journal of Organic Chemistry

Abbreviation

Eur. j. org. chem.

Publisher

Wiley-VCH

Journal Volumes

ISSN

1434-193X
1099-0690

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Filters

2007 - 200982020 - 20255
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Publications1 - 10 of 13
  • A topological view of isomeric dendrimers
    Item type: Journal Article
    Schubert, Dirk; Corda, Mirza; Lukin, Oleg; et al. (2008)
    European Journal of Organic Chemistry
  • Synthesis of a Spore Surface Pentasaccharide of Bacillus anthracis
    Item type: Journal Article
    Werz, Daniel B.; Adibekian, Alexander; Seeberger, Peter H. (2007)
    European Journal of Organic Chemistry
  • meso,meso-Linked and Triply Fused Diporphyrins with Mixed-Metal Ions
    Item type: Journal Article
    Fendt, Leslie-Anne; Fang, Hongjuan; Plonska-Brzezinska, Marta E.; et al. (2007)
    European Journal of Organic Chemistry
  • Catalyzing the Enantioselective Tail-to-Head Terpene Cyclization Inside Optically Active Hexameric Resorcin[4]arene Capsules: A Surprising Odd-Even Effect of the Catalyst
    Item type: Journal Article
    Persiani, Giacomo; Sokolova, Daria; Ivanov, Roman; et al. (2024)
    European Journal of Organic Chemistry
    Terpenes, created in Nature via tail-to-head terpene (THT) cyclizations, have long fascinated chemists due to their complex structures and biological activities. Recreating such THT cyclizations in the laboratory using man-made catalysts has been challenging. Especially difficult is performing the reaction in an enantioselective fashion, as the substrate is flexible and does not contain much functionality to form strong interactions with the chiral catalyst. This study explores the enantioselective THT cyclization inside hexameric capsules self-assembled from optically active resorcin[4]arene derivatives. An unexpected odd-even effect, where the enantioselectivity of the reaction depended on the length of the alkyl chain attached to the resorcin[4]arene capsule was uncovered. To our knowledge, this is the first example of an odd-even effect in the catalyst itself, and also the first instance in which this effect is related to the enantioselectivity of the reaction.
  • 1,3-Diethynylallenes
    Item type: Journal Article
    Wiel, Matthijs K.J. ter; Odermatt, Severin; Schanen, Patrick; et al. (2007)
    European Journal of Organic Chemistry
  • New Push-Pull Chromophores Featuring TCAQ (11,11,12,12-Tetracyano- 9,10-anthraquinodimethane) and Other Dicyanovinyl Acceptors
    Item type: Journal Article
    Bureš, Filip; Schweizer, W. Bernd; Boudon, Corinne; et al. (2008)
    European Journal of Organic Chemistry
  • Cationic vanadium(IV) complexes as efficient catalysts for Nazarov cyclizations
    Item type: Journal Article
    Walz, Irene; Bertogg, Andreas; Togni, Antonio (2007)
    European Journal of Organic Chemistry
  • Aryl Crown Ethers Based on d-Glucose Scaffold - Highly Selective Receptors of Amino Acid Ester Hydrochlorides
    Item type: Journal Article
    Chak, Man Him; Schnurr, Martin; Lewandowski, Bartosz (2023)
    European Journal of Organic Chemistry
    Amino acids are important biomolecules with a broad scope of applications in chemical and biological sciences. Their functions and properties depend on their absolute configuration. Therefore, methods for chiral recognition and separation of amino acids are highly sought after. For the purposes of diagnostic and medicinal applications chiral recognition of amino acids in water is particularly relevant. However synthetic receptors for enantioselective binding of amino acids in aqueous media are rare. Recently we reported a d-glucose-based crown ether for chiral recognition of amino acid esters in water. We achieved enantioselectivities towards amino acids with hydrophobic sidechains which were among the highest ever reported for a small molecule receptor. The binding affinities were however moderate. Herein we disclose analogs of that receptor, containing aryl functionalities in the crown ether fragment. The new receptors show considerably improved binding affinities for amino acid ester hydrochlorides in water, while retaining high enantio- or chemoselectivities.
  • Studies towards the Total Synthesis of Amycolamicin: A Chiral Auxiliary-Based Diels-Alder Approach towards the Decalin Core
    Item type: Journal Article
    Frossard, Thomas Maxime; Trapp, Nils; Altmann, Karl-Heinz (2022)
    European Journal of Organic Chemistry
    The stereoselective synthesis of (1S,2S,5R)-5-((4-methoxybenzyl)oxy)-2-methyl-8-methylene-1,2,4a,5,6,7,8,8a-octahy-dronaphthalene-1-carboxylic acid (2) is described, which comprises the bicyclic core structure of the natural product amycolamicin (1). The bicyclic ring-system was established via an intramolecular Diels-Alder reaction of a triene carrying a SuperQuat chiral auxiliary. The latter could be readily removed by methanolysis in excellent yield, which allowed for effective conversion of a hydroxy group at C(1) into the methylene group present in the natural product. The intramolecular Diels-Alder reaction could also be performed with a triene incorporating a classical, phenylalanine-derived Evans auxiliary, but the removal of the latter from the initial Diels-Alder product was hampered by competing attack of nucleophiles on the endocyclic carbonyl group in the oxazolidinone ring. Acid 2 could be converted into an acyl cyanide that features as a key advanced intermediate in one of the three total syntheses of amycolamicin reported to date.
  • Exploring the Chemistry of a Double-Stranded Cycle with the Carbon Skeleton of the Belt Region of the C84 Fullerene
    Item type: Journal Article
    Stuparu, Mihaiela; Lentz, Dieter; Rüegger, Heinz; et al. (2007)
    European Journal of Organic Chemistry
Publications1 - 10 of 13