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European Journal of Medicinal Chemistry [0223-5234]
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Microreviews
Reductive Cross-Coupling
Regioselective Reductive Cross-Coupling Reactions of Unsymmetrical Alkynes (p NA)Holly A. Reichard, Martin McLaughlin, Ming Z. Chen, Glenn C. MicalizioPublished Online: Nov 24 2009 1:15AMDOI: 10.1002/ejoc.200901094
Reductive cross-coupling chemistry is emerging as a powerful strategy for bimolecular C-C bond formation. A central issue in this area of chemistry is controlling site-selectivity (regioselectivity) in the convergent coupling process. Here, we discuss the state-of-the-art with respect to controlling regioselectivity in reductive cross-coupling chemistry of alkynes. The emphasis of this review is on bond construction, not the nature of the metal employed or whether or not the coupling process proceeds in a catalytic manner.
Abstract Full Text: PDF (Size: 1508K) Save Article
Organoindium Reagents
Recent Developments in Indium Metal and Its Salts in Organic Synthesis (p NA)J. S. Yadav, Aneesh Antony, Jimil George, Basi V. Subba ReddyPublished Online: Nov 6 2009 8:36AMDOI: 10.1002/ejoc.200900895
Indium chemistry is of great importance because of the huge potential of indium metal for induction of chirality through the use of chiral indium complexes, for the introduction of organic moieties through organoindium reagents, and for highly efficient reaction catalysis. A brief survey of recently reported reactions is illustrated with selected examples.
Abstract Full Text: PDF (Size: 477K) Save Article
Silylative Coupling
Silylative Coupling of Olefins with Vinylsilanes in the Synthesis of -Conjugated Double Bond Systems (p NA)Piotr Pawlu, Wiesaw Prukaa, Bogdan MarciniecPublished Online: Nov 3 2009 1:03PMDOI: 10.1002/ejoc.200900883
From simple vinylsilanes to complex -conjugated molecules: recent applications of sequential silylative coupling/desilylativecoupling methodology to the synthesis of functionalized arylvinyl derivatives are reviewed.
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Cycloaddition Reactions
The Diene Effect: The Design, Development, and Mechanistic Investigation of Metal-Catalyzed Diene-yne, Diene-ene, and Diene-allene [2+2+1] Cycloaddition Reactions (p NA)Mitchell P. Croatt, Paul A. WenderPublished Online: Oct 14 2009 1:49PMDOI: 10.1002/ejoc.200900929
This review covers the design and development aspects of the recently reported [2+2+1] reactions of dienes tethered to alkynes, alkenes, and allenes. The dienes in these reactions were found to behave very differently than other -systems and accelerated or enabled the respective [2+2+1] reactions. Additionally, mechanistic insights into these reactions and a synthetic application of the diene-ene [2+2+1] reaction are presented.
Abstract Full Text: PDF (Size: 1262K) Save Article
Short Communications
Natural Products
Bezerramycins A-C, Antiproliferative Phenoxazinones from Streptomyces griseus Featuring Carboxy, Carboxamide or Nitrile Substituents (p NA)Patrícia Bezerra Gomes, Markus Nett, Hans-Martin Dahse, Isabel Sattler, Karin Martin, Christian HertweckPublished Online: Dec 3 2009 7:25AMDOI: 10.1002/ejoc.200901206
Three phenoxazinones, which primarily differ in the carboxy, carboxamide and nitrile substituents at C-1, were isolated from a Streptomyces griseus strain. The cooccurence of the rare nitrile-functionalizedbezerramycin C with carboxy and carboxamide substituted congeners implies a biogenetic relationship.
Abstract Full Text: PDF (Size: 213K) Supporting informationSave Article
Friedel-Crafts Alkylations
Enantioselective Synthesis of Unsymmetrical Triarylmethanes by Chiral Brønsted Acids (p NA)Feng-Lai Sun, Xiao-Jian Zheng, Qing Gu, Qing-Li He, Shu-Li YouPublished Online: Nov 26 2009 11:49AMDOI: 10.1002/ejoc.200901164
Enantioselective synthesis of unsymmetrical triarylmethanes has been realized by a chiral Brønsted acid catalyzed Friedel-Crafts alkylation of electron-rich arenes with (3-indolyl)methanamines. With 5 mol-% of a newly developed chiral phosphoric acid, the enantioenriched unsymmetrical triarylmethanes were obtained in excellent yields with up to 91 % ee.
Abstract Full Text: PDF (Size: 172K) Supporting informationSave Article
Fluorinated Heterocycles
One-Pot Synthesis of Fluorinated 1-Benzoyl-3,4-dihydroisoquinolines from [2-(o-Alkynylphenyl)ethyl]amines by a Hydroamination/Oxidation Sequence (p NA)René Severin, Jessica Reimer, Sven DoyePublished Online: Nov 20 2009 9:21AMDOI: 10.1002/ejoc.200901034
Potentially antitumor-active fluorinated 1-benzoyl-3,4-dihydroisoquinolines can easily be synthesized by a new one-pot procedure from fluorinated [2-(o-alkynylphenyl)ethyl]amines in high yields. The main reaction steps are an initial Ti-catalyzed intramolecular alkyne hydroamination and a subsequent Pd-catalyzed oxidation.
Abstract Full Text: PDF (Size: 310K) Supporting informationSave Article
Natural Product Synthesis
Catalytic Asymmetric Synthesis of Mycolipenic and Mycolipanolic Acid (p NA)Bjorn ter Horst, Jeroen van Wermeskerken, Ben L. Feringa, Adriaan J. MinnaardPublished Online: Nov 18 2009 8:57AMDOI: 10.1002/ejoc.200901120
The first enantioselective total synthesis of mycolipenic acid and related mycolipanolic acid is described. The acids are prepared by an iterative enantioselective 1,4-addition protocol. The unsaturated system in mycolipenic acid and the propionate moiety in mycolipanolic acid are prepared by stereoselective Wittig olefination and stereoselective Evans aldol reaction, respectively.
Abstract Full Text: PDF (Size: 152K) Supporting informationSave Article
Domino Synthesis
Fluoride-Triggered Domino Reactions Involving Ammonium Acetylides and Carbonyl Compounds (p NA)David Tejedor, Sara López-Tosco, Gabriela Méndez-Abt, Fernando García-TelladoPublished Online: Nov 11 2009 10:58AMDOI: 10.1002/ejoc.200901082
Fluoride anions were found to trigger domino reactions capable of generating structurally diverse products from methyl propiolate and carbonyl derivatives. These processes construct different molecular architectures through three different autocatalytic reaction networks. Reactions are both bench-friendly and bench-economical: they are performed at room temperature, under an aerobic atmosphere, and by using nondried solvents.
Abstract Full Text: PDF (Size: 376K) Supporting informationSave Article
Organocatalysis
Remarkable Reaction Rate and Excellent Enantioselective Direct -Amination of Aldehydes with Azodicarboxylates Catalyzed by Pyrrolidinylcamphor-Derived Organocatalysts (p NA)Pang-Min Liu, Chihliang Chang, Raju Jannapu Reddy, Ying-Fang Ting, Hsuan-Hao Kuan, Kwunmin ChenPublished Online: Nov 5 2009 11:07AMDOI: 10.1002/ejoc.200901151
Remarkable reaction rate and excellentenantioselective direct -amination of aldehydes with various azodicarboxylates was catalyzed by pyrrolidinylcamphor organocatalyst 2a (5 mol-%) to provide the desired aminated products with excellent chemical yield and enantioselectivity (up to >99 % ee) at 0 °C in CH2Cl2.
Abstract Full Text: PDF (Size: 185K) Supporting informationSave Article
Full Papers
Bifunctional Antioxidants
A Phenolic Antioxidant Releasing Nitric Oxide on Demand (p NA)Elisa Vittorino, Salvatore SortinoPublished Online: Dec 4 2009 6:36AMDOI: 10.1002/ejoc.200901207
We have designed and synthesized, by a very simple procedure, a water-soluble molecular conjugate that combines radical scavenging properties to the delivery of nitric oxide in a way exclusively controlled by visible light external stimuli.
Abstract Full Text: PDF (Size: 586K) Save Article
Nitrogen Heterocycles
Versatility of Substituted 1-Formyl-9H--carbolines for the Synthesis of New Fused -Carbolines via Intramolecular 1,3-Dipolar Cycloaddition (p NA)Virender Singh, Samiran Hutait, Subhasish Biswas, Sanjay BatraPublished Online: Dec 4 2009 6:36AMDOI: 10.1002/ejoc.200901166
A simple route to the synthesis of several ring-fused -carbolines through 1-formyl-9H--carbolines using 1,3-dipolar cycloaddition as the key-step is reported.
Abstract Full Text: PDF (Size: 275K) Supporting informationSave Article
Nucleophilic Trifluoromethylation
Enantiopure 2-(Trifluoromethyl)-1,2,3,4-tetrahydronaphthalene-1,2-diols from a Tartaric Acid Derived Scaffold (p NA)Fabien Massicot, Jean Nonnenmacher, Fabienne Grellepois, Charles PortellaPublished Online: Dec 3 2009 7:25AMDOI: 10.1002/ejoc.200901153
The enantiopure stereoisomers of the title compound were prepared and characterized, starting from a tartaric acid derived keto amide.
Abstract Full Text: PDF (Size: 297K) Save Article
Antioxidant Models
A Water-Soluble Cyclic Selenide with Enhanced Glutathione Peroxidase-Like Catalytic Activities (p NA)Fumio Kumakura, Beena Mishra, K. Indira Priyadarsini, Michio IwaokaPublished Online: Dec 3 2009 7:25AMDOI: 10.1002/ejoc.200901114
Water-soluble cyclic selenide 1 exhibited higher GPx-like catalytic activities than the linear selenide analog in the reaction of H2O2 with mono-, di-, and polythiol substrates. The enhanced catalytic activities can be ascribed to the cyclic structure, which elevates the HOMO energy level of 1 and makes the selenium atom more exposed to the surroundings.
Abstract Full Text: PDF (Size: 685K) Supporting informationSave Article
Supramolecular Chemistry
Enhancing the Reactivity of an Electrophilic Barbiturate Dye by Cooperative Hydrogen Bonding (p NA)Mirko Bauer, Stefan SpangePublished Online: Dec 3 2009 7:25AMDOI: 10.1002/ejoc.200901066
For the first time it is demonstrated that it is possible to influence the reactivity of a neutral electrophile which possesses a hydrogen bonding motif by using a complementary receptor: Upon complexation of BA1 with the receptor DAC both the electrophilicity and the Lewis acidity of BA1 are markedly increased.
Abstract Full Text: PDF (Size: 468K) Supporting informationSave Article
Natural Products Chemistry
Keronopsamides, a New Class of Pigments from Marine Ciliates (p NA)Graziano Guella, Rita Frassanito, Ines Mancini, Tommaso Sandron, Letizia Modeo, Franco Verni, Fernando Dini, Giulio PetroniPublished Online: Dec 3 2009 7:25AMDOI: 10.1002/ejoc.200900905
Keronopsamides A-C, isolated from a cell culture of the marine ciliate Pseudokeronopsis riccii are new pigments based on an unprecedented amide linkage between a basic bromophenol moiety and an alkyl-substituted dibromopyrrole. The relative stabilities of tautomeric forms and rotational conformers have been investigated by NMR techniques and DFT-based computations.
Abstract Full Text: PDF (Size: 275K) Save Article
Fullerene Chemistry
Fullerene Unsymmetrical Bis-Adducts as Models for Novel Peptidomimetics (p NA)Dragana Milic, Maurizio PratoPublished Online: Dec 3 2009 7:25AMDOI: 10.1002/ejoc.200900791
Two classes of unsymmetrical, orthogonally protected bis-fulleropyrrolidinic amino acids have been designed as model compounds for novel fulleropeptidomimetics. The synthesis of NHFmoc/CO2tBu and NHBoc/CO2Me fulleropyrrolidinic couples is presented. All the trans as well as the equatorial (e and e) isomers were separated and fully characterized by NMR spectroscopy and mass spectrometry.
Abstract Full Text: PDF (Size: 393K) Save Article
Functionalized Atropisomeric Biaryls
Use of the Diels-Alder Cycloaddition of Tetracyclone and Internal Aryl Acetylenes for the Synthesis of Functionalized Atropisomeric Biaryls (p NA)Marko Hapke, Andrey Gutnov, Nico Weding, Anke Spannenberg, Christine Fischer, Christian Benkhäuser-Schunk, Barbara HellerPublished Online: Dec 2 2009 6:20AMDOI: 10.1002/ejoc.200901080
The cycloaddition of tetracyclone and internal aryl acetylenes successfully yielded atropisomeric biaryls in mostly high yields when the acetylenes were carrying electron-accepting substituents. The resolution ofthe atropisomers via diastereomers was exemplified, leading to the isolation of the enantiomerically pure phosphane oxides and subsequently phosphanes.
Abstract Full Text: PDF (Size: 253K) Supporting informationSave Article
On-Column Reactions
Solid-Phase Reactive Chromatography (SPRC): A New Methodology for Wittig and Horner-Emmons Reactions on a Column under Microwave Irradiation (p NA)Saada C. Dakdouki, Didier Villemin, Nathalie BarPublished Online: Dec 2 2009 6:20AMDOI: 10.1002/ejoc.200901032
The synthesis of some natural bioactive compounds, including (E)-stilbenes, alkylideneresorcinols, and 5-aryl-2,4-pentadienoates, over a column of alumina-KF under microwave irradiation was investigated by using the Wittig and Horner-Emmons reactions.
Abstract Full Text: PDF (Size: 298K) Save Article
Diastereoselective Grignard Reactions
Reactions of the Bornyl and Fenchyl Grignard Reagent with Chlorophosphanes - Diastereoselectivity and Mechanistic Implications (p NA)Jens Beckmann, Alexandra SchütrumpfPublished Online: Dec 2 2009 6:20AMDOI: 10.1002/ejoc.200900908
The reaction of the fenchyl Grignard reagent (ratio endo/exo = 20:80) or the epimerized fenchyl Grignard reagent (ratio endo/exo = 80:20) with (NEt2)2PCl gave rise to a mixture of - and -fenchylbis(diethylamino)phosphane with an endo/exo ratio of 6:94 regardless of the original endo/exo ratio. The results of the substitution reactions are consistent with a SET mechanism involving the fenchyl radical as intermediate.
Abstract Full Text: PDF (Size: 754K) Supporting informationSave Article
Porphyrins
Synthesis of meso-Substituted ABCD-Type Porphyrins by Functionalization Reactions (p NA)Mathias O. Senge, Yasser M. Shaker, Monica Pintea, Claudia Ryppa, Sabine S. Hatscher, Aoife Ryan, Yulia SergeevaPublished Online: Dec 1 2009 10:04AMDOI: 10.1002/ejoc.200901113
A comprehensive study of contemporary synthetic methods by using organolithium and Pd-catalyzed C-C coupling reactions for ABCD-porphyrins reveals that it is now possible to prepare almost any desired meso-substituted porphyrin.
Abstract Full Text: PDF (Size: 970K) Supporting informationSave Article
Optically Active Heterocycles
Synthesis of Optically Active Heterocyclic Compounds by Preparation of 1,3-Dinitro Derivatives and Enzymatic Enantioselective Desymmetrization of Prochiral Diamines (p NA)Nicolás Ríos-Lombardía, Eduardo Busto, Vicente Gotor-Fernández, Vicente GotorPublished Online: Dec 1 2009 10:04AMDOI: 10.1002/ejoc.200900875
A general synthetic methodology for the preparation of novel monocarbamates in good to high enantiomeric excesses (70-90 % ee) is described. Thus, commercially available aldehydes have been transformedinto 1,3-dinitro compounds, which were hydrogenated by using platinum oxide as the catalyst and then enantioselectively desymmetrized by using Pseudomonas cepacia lipase as the biocatalyst.
Abstract Full Text: PDF (Size: 270K) Supporting informationSave Article
Fluorescent Probes
Synthesis and Photophysical Studies of New Fluorescent Indole Derivatives Obtained from -Bromodehydroamino Acids - Interaction with Fluoride Anions (p NA)Goreti Pereira, Elisabete M. S. Castanheira, Paula M. T. Ferreira, Maria-João R. P. QueirozPublished Online: Dec 1 2009 10:04AMDOI: 10.1002/ejoc.200900737
New fluorescent indole derivatives were synthesised from -bromodehydroamino acid derivatives and aryl boronic acids by using a Suzuki coupling reaction followed by a C-N intramolecular cyclisation reaction. The photophysical properties of the new indole derivatives indicate their potential use as fluorescent probes. The interaction of these compounds with fluoride anion was studied.
Abstract Full Text: PDF (Size: 1308K) Supporting informationSave Article
Grape Pigments
Physicochemical Studies of New Anthocyano-Ellagitannin Hybrid Pigments: About the Origin of the Influence of Oak C-Glycosidic Ellagitannins on Wine Color (p NA)Stefan Chassaing, Dorothée Lefeuvre, Rémi Jacquet, Michael Jourdes, Laurent Ducasse, Stéphanie Galland, Axelle Grelard, Cédric Saucier, Pierre-Louis Teissedre, Olivier Dangles, Stéphane QuideauPublished Online: Nov 30 2009 3:02PMDOI: 10.1002/ejoc.200901133
Purple-colored anthocyano-ellagitannins, derived from the oak ellagitannin vescalagin and the red-colored grape pigmentsoenin and malvidin, are likely to play a role in the modulation of wine color during aging in oak barrels.
Abstract Full Text: PDF (Size: 1156K) Supporting informationSave Article
Gold-Catalyzed Transformations
Synthesis of Bicyclic Ethers by a Gold/Palladium/Gold-Catalyzed Cyclization/Cross Coupling Sequence (p NA)Birgit Gockel, Norbert KrausePublished Online: Nov 30 2009 3:02PMDOI: 10.1002/ejoc.200901010
The stereoselective gold-catalyzed 6-endo cyclization of various -hydroxyallenes in the presence of N-iodosuccinimide affords iodinated dihydropyrans in good yield. Subsequent functionalization by palladium-catalyzed cross coupling opens an access to -hydroxyallenes that are converted in a second gold-catalyzed cyclization into bicyclic ethers which occur in various natural products.
Abstract Full Text: PDF (Size: 254K) Supporting informationSave Article
Green Toadstool Pigment
Cristatomentin, a Green Pigment of Mixed Biogenetic Origin from Albatrellus cristatus (Basidiomycetes) (p NA)Barbara Koch, Claus Kilpert, Wolfgang SteglichPublished Online: Nov 30 2009 3:02PMDOI: 10.1002/ejoc.200900718
The structure of cristatomentin has been elucidated by MS studies and comparison of its NMR spectrum with those of cristatic acid and albatrellin. The furylbenzoquinone chromophore of cristatomentin may arise from cristatic acid and 2-O-acetylatromentin, which co-occur with the title compound in the fungus.
Abstract Full Text: PDF (Size: 354K) Save Article
Multisubstituted Pyrroles
A New Method for the Synthesis of Multisubstituted Pyrroles of Biological Interest by Double Nucleophilic Addition to ,-Unsaturated Imines (p NA)Atsushi Takahashi, Shiho Kawai, Iwao Hachiya, Makoto ShimizuPublished Online: Nov 27 2009 5:57AMDOI: 10.1002/ejoc.200901055
The double nucleophilic addition reactions of dialkoxy ketene silyl acetals proceeded with ,-unsaturated imines to give 1,4-and 1,2-double addition products, and their subsequent transformations afforded multisubstituted pyrroles in good yields.
Abstract Full Text: PDF (Size: 312K) Supporting informationSave Article
Multifunctional Peptide Dendrimers
A Versatile, Modular Platform for Multivalent Peptide Ligands Based on a Dendritic Wedge (p NA)Edith H. M. Lempens, Brett A. Helms, Andrea R. Bayles, Maarten Merkx, E. W. MeijerPublished Online: Nov 27 2009 5:57AMDOI: 10.1002/ejoc.200901045
An efficient, modular and broadly applicable strategy is presented for the synthesis of multivalent and multifunctional peptide dendrimers. The scope of the method is demonstrated by introduction of a variety ofpopular targeting peptides at the periphery and other biologically relevant groups at the focal point of ABn-type (n = 2-5) dendrons.
Abstract Full Text: PDF (Size: 581K) Supporting informationSave Article
Natural Product Synthesis
Total Synthesis of a Diarylheptanoid, Rhoiptelol B (p NA)Chada Raji Reddy, Nagavaram Narsimha Rao, Boinapally SrikanthPublished Online: Nov 27 2009 5:57AMDOI: 10.1002/ejoc.200901041
The first total synthesis of rhoiptelol B has been achieved in 15 steps in a stereoselective and convergent fashion. The key steps used were Keck allylation, Jacobson resolution, lithium-mediated aldol reaction and reductive etherification for the generation of required chiral centers.
Abstract Full Text: PDF (Size: 293K) Save Article
-Lactam Chemistry
Synthesis of 3,4-Fused Bicyclic -Lactams and Their Transformation into Methyl cis-3-Aminotetrahydrofuran-2-carboxylates (p NA)Erika Leemans, Matthias D'hooghe, Yves Dejaegher, Karl W. Törnroos, Norbert De KimpePublished Online: Nov 26 2009 11:49AMDOI: 10.1002/ejoc.200901110
cis-3-Benzyloxy-4-(2-bromo-1,1-dimethylethyl)azetidin-2-ones were transformed into novel cis-2-oxa-6-azabicyclo[3.2.0]heptan-7-ones by a two-step procedure. Thelatter cis-2-oxa-6-azabicyclo[3.2.0]heptan-7-ones were subsequently converted into cis-3-aminotetrahydrofuran-2-carboxylates through acidic methanolysis.
Abstract Full Text: PDF (Size: 248K) Supporting informationSave Article
Labelled Tropane Alkaloids
A Short and Efficient Synthesis of Bridgehead Mono- and Dideuteriated Tropinones (p NA)Anaïs Fournial, Tsiresy Ranaivondrambola, Monique Mathé-Allainmat, Richard J. Robins, Jacques LebretonPublished Online: Nov 26 2009 11:49AMDOI: 10.1002/ejoc.200901018
An efficient synthesis of 1,5-dideuterio- and racemic 1-deuteriotropinone is described in which high levels of deuterium are incorporated from the corresponding di- and mono-labelled 2,5-dibutoxytetrahydrofuran, respectively, at either one or both of the bridgehead carbons C-1 and C-5.
Abstract Full Text: PDF (Size: 256K) Supporting informationSave Article
Phenanthro-indolizidine Alkaloids
Efficient and Chirally Specific Synthesis of Phenanthro-Indolizidine Alkaloids by Parham-Type Cycloacylation (p NA)Ziwen Wang, Zheng Li, Kailiang Wang, Qingmin WangPublished Online: Nov 25 2009 12:47PMDOI: 10.1002/ejoc.200900920
A series of enantiopure phenanthro-indolizidine alkaloids have been synthesized in excellent overall yields and with very high ee values with Parham-type cycloacylationas the key step. The large-scale preparation of enantiomerically pure alkaloids is now feasible.
Abstract Full Text: PDF (Size: 417K) Supporting informationSave Article
Artificial Enzymes
Amino-Acetone-Bridged Cyclodextrins - Artificial Alcohol Oxidases (p NA)Lavinia G. Marinescu, Elisa G. Doyagüez, Marta Petrillo, Alfonso Fernández-Mayoralas, Mikael BolsPublished Online: Nov 24 2009 1:15AMDOI: 10.1002/ejoc.200901099
Three amino-acetone-bridged cyclodextrins have been synthesized and kinetic studies revealed very good substrate-selective enzymatic catalysis for the oxidation of benzyl alcohols with a rate increase of up to 18500 under neutral conditions at room temperature using hydrogen peroxide as co-oxidant. They also exhibit stereoselectivity in the oxidation of different enantiomers.
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Heterocyclic Antitumor Agents
A Simple One-Pot Synthesis of New Imidazol-2-yl-1H-quinolin-2-ones from the Direct Reaction of 2-Chloroquinolin-3-carbaldehyde with Aromatic o-Diamines (p NA)Rodrigo Abonia, Juan Castillo, Paola Cuervo, Braulio Insuasty, Jairo Quiroga, Alejandro Ortíz, Manuel Nogueras, Justo CoboPublished Online: Nov 24 2009 1:15AMDOI: 10.1002/ejoc.200901014
We implemented an efficient, one-step procedure for the direct synthesis of new imidazol-2-yl-1H-quinolin-2-ones from the reaction of 2-chloroquinolin-3-carbaldehydewith aromatic o-diamines using Amberlyst®-15 as catalyst. This approach involved simultaneous C-Cl hydrolysis and condensation processes in the same pot.
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Dye-Sensitized Solar Cells
Dye-Sensitized Solar Cells Based on a Novel Fluorescent Dye with a Pyridine Ring and a Pyridinium Dye with the Pyridinium Ring Forming Strong Interactions with Nanocrystalline TiO2 Films (p NA)Yousuke Ooyama, Shogo Inoue, Risa Asada, Genta Ito, Kohei Kushimoto, Kenji Komaguchi, Ichiro Imae, Yutaka HarimaPublished Online: Nov 24 2009 1:15AMDOI: 10.1002/ejoc.200900983
As a new-type donor-acceptor -conjugated (D--A) dye capable of forming a strong interaction between the electron-acceptor moiety of the sensitizer and a TiO2 surface, the fluorescent dye OH11, with a pyridine ring as the electron-accepting group, has been designed and synthesized as a photosensitizer for use in dye-sensitized solar cells (DSSCs).
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Asymmetric Tandem Process
An Asymmetric Tandem Conjugative Addition-Intramolecular Cyclisation Process to Provide Functionalised 3,6-Dihydropyrans and 4,5-Epoxytetrahydropyrans (p NA)Silvia Catalán-Muñoz, Constanze A. Müller, Steven V. LeyPublished Online: Nov 20 2009 9:21AMDOI: 10.1002/ejoc.200901145
An efficient and convenient two-step synthesis of enantiomerically enriched dihydropyran and epoxytetrahydropyran derivatives is described. The key step involvesa tandem conjugative addition-intramolecular cyclisation/epoxidation process from easily available enantiomerically pure -hydroxy aldehydes.
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Asymmetric Catalysis
Enantioselective Fujiwara-Moritani Indole and Pyrrole Annulations Catalyzed by Chiral Palladium(II)-NicOx Complexes (p NA)Julia A. Schiffner, Thorsten H. Wöste, Martin OestreichPublished Online: Nov 20 2009 9:21AMDOI: 10.1002/ejoc.200901129
The long known Fujiwara-Moritani arylation of alkenes, an oxidative palladium(II) catalysis, is finally accomplished in an asymmetric sense. C-H bond activation at indoles and pyrroles followed by conventional Heck-type C-C bond formation allows for enantioselective construction of a congested quaternary carbon atom.
Abstract Full Text: PDF (Size: 406K) Supporting informationSave Article
Carbohydrate Recognition
Selective Recognition of -Mannosides by Synthetic Tripodal Receptors: A 3D View of the Recognition Mode by NMR (p NA)Ana Ardá, Chiara Venturi, Cristina Nativi, Oscar Francesconi, F. Javier Cañada, Jesús Jiménez-Barbero, Stefano RoelensPublished Online: Nov 20 2009 9:21AMDOI: 10.1002/ejoc.200901024
A 3D model of the complex of a synthetic tripodal receptor with octyl -D-mannoside based on molecular mechanics calculations and NMR experimental data is proposed. The structure explains the observed selectivity for -mannosyl in terms of hydrogen bonding, intermolecular van der Waals interactions and conformational bias
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Pd-catalyzed Cyclization
Synthesis of Novel Substituted Phenanthrenes and Polycyclic Heteroarenes by Pd-Catalyzed, Direct, Intramolecular Arylation/Heteroarylation (p NA)Ashok K. Yadav, Hiriyakkanavar Ila, Hiriyakkanavar JunjappaPublished Online: Nov 18 2009 8:57AMDOI: 10.1002/ejoc.200901036
An efficient route to substituted phenanthrenes and polycyclic heteroarenes by a direct, Pd-catalyzed, intramolecular arylation/heteroarylation of 2-(2-bromoaryl/heteroaryl)-3-(aryl/heteroaryl)-3-(methylthio)acrylonitriles has been reported.
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Amidation of Aldehydes
Cyclopentadienyl-Free Rare-Earth Metal Amides [{(CH2SiMe2){(2,6-iPr2C6H3)N}2}Ln{N(SiMe3)2}(THF)] as Highly Efficient Versatile Catalysts for C-C and C-N Bond Formation (p NA)Yunjun Wu, Shaowu Wang, Lijun Zhang, Gaosheng Yang, Xiancui Zhu, Zhihong Zhou, Hong Zhu, Shihong WuPublished Online: Nov 18 2009 8:57AMDOI: 10.1002/ejoc.200901015
Cyclopentadienyl-free rare-earth metal amides [{(CH2SiMe2){(2,6-iPr2C6H3)N}2}Ln{N(SiMe3)2}(THF)] have been found to be versatile catalysts for C-N and C-C bond formation.
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Synthetic Monophosphoryl Lipid A
Chemical Synthesis and Proinflammatory Responses of Monophosphoryl Lipid A Adjuvant Candidates (p NA)Kaustabh K. Maiti, Michael DeCastro, Abu-Baker M. Abdel-Aal El-Sayed, Matthew I. Foote, Margreet A. Wolfert, Geert-Jan BoonsPublished Online: Nov 18 2009 8:57AMDOI: 10.1002/ejoc.200900973
A methylated monophosphoryl lipid A derivative exhibits reduced potency and efficacy for cytokine production making it anattractive candidate for adjuvant development.
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Heterocyclic Chemistry
DFT Study on Tautomerism of Dihydro-2H-1,5-benzodiazepin-2-ones and Dihydro-2H-1,5-benzodiazepine-2-thiones (p NA)Sergiy I. Okovytyy, Liudmyla K. Sviatenko, Alexandr A. Gaponov, Liliya I. Kasyan, Igor N. Tarabara, Jerzy LeszczynskiPublished Online: Nov 18 2009 8:57AMDOI: 10.1002/ejoc.200900689
An exhaustive study of tautomerization in three kinds of dihydro-1,5-benzodiazepin(e)-2-(thi)one systems through theoretical calculations is reported.
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Trifluoromethylated Enamines
A Cascade Approach to Captodative Trifluoromethylated Enamines or Vinylogous Guanidinium Salts: Aromatic Substituents as Switches of Reaction Direction (p NA)Alexander Yu. Rulev, Vasiliy M. Muzalevskiy, Evgeniy V. Kondrashov, Igor A. Ushakov, Aleksey V. Shastin, Elizabeth S. Balenkova, Günter Haufe, Valentine G. NenajdenkoPublished Online: Nov 17 2009 11:04AMDOI: 10.1002/ejoc.200900926
The electronic natures of the aromatic substituents on -halo--(trifluoromethyl)styrenes govern the outcomes of their reactions with nitrogen nucleophiles bearing primary amino groups, the reaction products being either captodative trifluoromethylated enamines or vinylogous guanidinium salts.
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Green Chemistry
Green Synthesis of Vicinal Dithioethers and Alkenyl Thioethers from the Reaction of Alkynes and Thiols in Water (p NA)Zhuang Jin, Bo Xu, Gerald B. HammondPublished Online: Nov 17 2009 1:03AMDOI: 10.1002/ejoc.200901101
Alkynes reacted with thiols in water to give vicinal dithioethers, and non-terminal propargyl alcohols reacted with phenyl thiols to produce a highly regio and stereoselective monohydrothiolation product, (E)-alkenyl thioether.
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Baker's Yeast Stereoselectivity
Baker's Yeast Reduction of -Hydroxy Ketones (p NA)Daniela Acetti, Elisabetta Brenna, Claudio Fuganti, Francesco G. Gatti, Stefano SerraPublished Online: Nov 17 2009 1:03AMDOI: 10.1002/ejoc.200901006
Stereoselective reduction of hydroxy ketones by baker's yeast was exploited for concomitant control of the configurations of 1,3-diol triads.
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Cyclooligomerization of Alkynes
Cyclooligomerization of Mono- and Diazulenylethynes Catalyzed by Transition Metal Complexes (p NA)Ahmed H. M. Elwahy, Klaus HafnerPublished Online: Nov 17 2009 1:03AMDOI: 10.1002/ejoc.200900946
Co-catalyzed cyclooligomerization of ethynylazulenes as well as diazulenylethynes to the corresponding azulenyl-substituted cyclobutadienes and benzenes is described.
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Blue OLED Material
Synthesis and Photophysical Properties of Pyrene-Based Light-Emitting Monomers: Highly Pure-Blue-Fluorescent, Cruciform-Shaped Architectures (p NA)Jian-yong Hu, Masanao Era, Mark R. J. Elsegood, Takehiko YamatoPublished Online: Nov 11 2009 10:58AMDOI: 10.1002/ejoc.200900806
Cruciform-shaped, conjugated monomers based on pyrene were successfully synthesised by a Sonogashira coupling reaction. Both single-crystal X-ray analysis andphotophysical studies strongly indicate their promising use as blue-emitting materials in organic light-emitting diodes (OLEDs).
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Fe-Promoted CC Bond Formation
FeX3-Promoted Intermolecular Addition of Benzylic Alcohols to Aromatic Alkynes: A Mild and Efficient Strategy for the Synthesis of Alkenyl Halides (p NA)Kai Ren, Min Wang, Lei WangPublished Online: Nov 9 2009 11:18AMDOI: 10.1002/ejoc.200901020
A convenient, effective, mild and simple strategy has been developed for the synthesis of alkenyl halides by the intermolecular addition of benzylic alcohols to aromatic alkynes in the presence of iron(III) bromide or chloride. Alkenyl bromides andchlorides were obtained with high regio- and stereoselectivity (E/Z up to 99:1) in good to excellent yields in 0.5-1 h under mild reaction conditions.
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Hydrosoluble Triazatruxenes
Study of a Convenient Method for the Preparation of Hydrosoluble Fluorescent Triazatruxene Derivatives (p NA)Marco Franceschin, Luca Ginnari-Satriani, Antonello Alvino, Giancarlo Ortaggi, Armandodoriano BiancoPublished Online: Nov 6 2009 8:36AMDOI: 10.1002/ejoc.200900869
In this paper, we compare different synthetic routes for the preparation of hydrophilic triazatruxene derivatives and showthat they are fluorescent both in organic solvents and in water.
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Electrophilic Reactions
Highly Selective Synthesis of [(Z)-3-Chloro-2-(phenylselanyl)-1-alkenyl]phosphonates and 2-Ethoxy-4-(phenylselanyl)-2,5-dihydro-1,2-oxaphosphole 2-Oxides by Electrophilic Reaction of 1,2-Alkadienylphosphonates with PhSeCl (p NA)Guangke He, Yihua Yu, Chunling Fu, Shengming MaPublished Online: Nov 5 2009 11:07AMDOI: 10.1002/ejoc.200900913
The reactions of monosubstituted 1,2-alkadienylphosphonates with PhSeCl in THF or dioxane/H2O (10:1) afforded [(Z)-3-chloro-2-(phenylselanyl)-1-alkenyl]phosphonates with a very high (Z) stereoselectivity, whereasthe same reaction with di- and trisubstituted allenylphosphonates afforded 2-ethoxy-4-(phenylselanyl)-2,5-dihydro-1,2-oxaphosphole 2-oxides exclusively.
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Molecular Electronics
Synthesis of Rotationally Restricted and Modular Biphenyl Building Blocks (p NA)David Vonlanthen, Jürgen Rotzler, Markus Neuburger, Marcel MayorPublished Online: Nov 4 2009 9:44AMDOI: 10.1002/ejoc.200900805
The synthesis of a series of modular biphenyl building blocks with restricted torsion angles is described. Short alkyl bridges dictate the conformation and provide rigid rod-type structures with well-defined backbone conjugation.
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Corrections
Efficient Synthesis of -Glycosphingolipids by Reaction of Stannylceramides with Glycosyl Iodides Promoted by TBAI/AW 300 Molecular Sieves (p NA)José Antonio Morales-Serna, Yolanda Díaz, M. Isabel Matheu, Sergio CastillónPublished Online: Nov 27 2009 5:57AMDOI: 10.1002/ejoc.200901247
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