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European Journal of Organic Chemistry
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Editor: Haymo Ross, Deputy Editor: Susan Wilkinson
Online ISSN: 1099-0690
Associated Title(s): Advanced Synthesis & Catalysis, Asian Journal of Organic Chemistry
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| October 19, 2012 EurBest in EurJOC: Tandem Aldol Condensation/Platinacycle-Catalyzed Addition Reactions of Aldehydes, Methyl Ketones, and Arylboronic Acids
The aldol condensation of aldehydes with methyl ketones was successfully combined with the platinacycle-catalyzed addition reactions of arylboronic acids in a tandem fashion. A variety of β-arylated ketones was obtained in good to excellent yields. October 19, 2012 EurBest in EurJOC: Potassium 4-Iodylbenzenesulfonate: Preparation, Structure, and Application as a Reagent for Oxidative Iodination of Arenes
October 10, 2012 EurBest in EurJOC: On the Reactivity and Selectivity of Galacturonic Acid Lactones
The reactivity and stereoselectivity of a galacturonic acid 3,6-lactone thioglycosyl donor has been investigated by using thiophilic activator systems. The reactivity of the thioglycosides depends on the activator system used. The stereoselectivity arises from preactivation of the glycosylation system, giving rise to α-selective glycosylation, whereas in situ activation gives the β-product. October 10, 2012 EurBest in EurJOC: Phosphane-Catalyzed [4+2] Annulation of Allenoates with Ketimines: Synthesis of Sultam-Fused Tetrahydropyridines
Cyclic ketimines were successfully used as electrophiles in phosphane-catalyzed [4+2] annulation reactions with ethyl 2-methyl-2,3-butadienoate to give the corresponding highly substituted tetrahydropyridine derivatives in moderate to good yields (55–73 %), and with moderate to excellent regioselectivity. September 18, 2012 EurBest in EurJOC: Lyngbyabellins K–N from Two Palmyra Atoll Collections of the Marine Cyanobacterium Moorea bouillonii
Two independent collections of the marine cyanobacterium Moorea bouillonii led to the isolation of five lipopeptides of the lyngbyabellin structure class. Their structures were elucidated by various spectroscopy, synthesis, and chromatography techniques. Lyngbyabellin N showed strong cytotoxic activity against the HCT116 colon cancer cell line (IC50 = 40.9 ± 3.3 nM). September 17, 2012 EurBest in EurJOC: Arylamine-Modified Thiazoles as Donor–Acceptor Dyes: Quantum Chemical Evaluation of the Charge-Transfer Process and Testing as Ligands in Ruthenium(II) Complexes
Several 4-hydroxy-1,3-thiazole-based chromophores bearing different arylamine donor and N-heterocyclic acceptor moieties were synthesized and their electronic properties were investigated experimentally and theoretically (DFT and TDDFT). The nature of the charge-transfer transition was identified. Additionally, the dyes were applied as light-harvesting ligands in heteroleptic RuII complexes. September 11, 2012 EurBest in EurJOC: General and Efficient α-Oxygenation of Carbonyl Compounds by TEMPO Induced by Single-Electron-Transfer Oxidation of Their Enolates
The oxygenation of enolates proves to be the most general and effective methodology for the synthesis of O-protected α-oxy carbonyl compounds and nitriles A. The scope and limitations of the electron-transfer-induced radical coupling reaction with TEMPO are presented. The reaction pathways are outlined. Methods for the deprotection to α-hydroxy carbonyl compounds B are provided and discussed. September 11, 2012 EurBest in EurJOC: Blurring the Boundary between Bio- and Geohopanoids: Plakohopanoid, a C32 Biohopanoid Ester from Plakortis cf. lita
Plakohopanoid is a new type of hopanoid composed of a C32 hopanoic acid ester linked to a mannosyl-myo-inositol. It is probably produced by bacterial symbionts of Plakortis cf. lita. The existence of a biosynthetic pathway to the C32 hopanoic acid shows that this compound should not be necessarily considered to be a geohopanoid. September 05, 2012 EurBest in EurJOC: Special Electronic Structure and Extended Supramolecular Oligomerization of Anionic 1,4-Dicorannulenylbenzene
The reduction of 1,4-dicorannulenylbenzene is strongly affected by the benzene spacer, yielding an unexpected triplet ground state of the dianion and an octaanion that self-assembles into highly charged supramolecular oligomers that are longer than previously observed dicorannulenyl oligomers. September 04, 2012 EurBest in EurJOC: Sesquiterpenoids from Common Ragweed (Ambrosia artemisiifolia L.), an Invasive Biological Polluter
Eight novel sesquiterpenoids were isolated from the aerial parts of Ambrosia artemisiifolia, an invasive weed whose pollen is responsible for severe allergic reactions. α,β-Unsaturated carbonyl derivatives were present in all aerial parts of the plant, and their reaction with thiols was correlated with the activation of TRPA1, a polymodal sensor involved in airways sensory irritation. August 29, 2012 EurBest in EurJOC: Controllable Regioselective Construction of Both Functional α-Methylene-β- and -γ-amino Acid Derivatives Through an Organocatalyzed Tandem Allylic Alkylation and Amination
A controllable regioselective allylic alkylation and amination reaction has been developed by using α-amino nitriles for the highly selective construction of β- and γ-amino acid derivatives incorporating multiple functional groups. Subsequent multicomponent tandem reactions and transformations of the densely functionalized products were shown to readily afford a range of useful building blocks. August 21, 2012 EurBest in EurJOC: Synthesis of SHIP1-Activating Analogs of the Sponge Meroterpenoid Pelorol
Two biomimetic routes have been used to synthesize analogs of the SHIP1-activating sponge meroterpenoid pelorol (1) in high ee. Resorcinol analog 18 is the most effective SHIP1-activating pelorol analog made to date and racemic 28•HCl, an amino analog, activates SHIP1 in vitro, and has effective antiinflammatory activity in a mouse model (ED50 ≈ 0.1 mg/kg). | October 19, 2012 October 19, 2012 October 10, 2012 October 10, 2012 September 18, 2012 September 11, 2012 September 11, 2012 September 05, 2012 September 04, 2012 August 21, 2012 August 07, 2012 July 31, 2012 July 24, 2012 July 17, 2012 July 04, 2012 June 12, 2012 June 05, 2012 May 22, 2012 May 22, 2012 May 15, 2012 May 08, 2012 April 30, 2012 |
A new hypervalent iodine(V) compound, potassium 4-iodylbenzenesulfonate, was prepared by oxidation of 4-iodobenzenesulfonic acid with Oxone in water. This new reagent promises many practical applications as a thermally stable, water-soluble and recyclable hypervalent iodine oxidant, particularly useful for oxidative iodination of aromatic substrates.
![EurBest in EurJOC: Phosphane-Catalyzed [4+2] Annulation of Allenoates with Ketimines: Synthesis of Sultam-Fused Tetrahydropyridines](ejoc-201200747.jpg)
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