Download pdf - Graphical Abstract: Eur. J. Org. Chem. 14/2005

Papers available ahead of print in Early View at www.interscience.wiley.com

Issue 14/2005

Pages 2851�3142

COVER PICTURE

The cover picture shows the X-ray crystal structures of thecompounds obtained by the alkylation of a conjugated por-phyrinogen precursor at its macrocyclic nitrogen atoms with2-(methylenenaphthyl) groups. The presence of the N-alkylgroups introduces intermolecular π�π stacking interactionswhich culminate in a 1-dimensional stacked array for thefully N-substituted derivative. The N-alkylation enhances theability of the compounds to form anion radical and cationradical species and permits “tuning” of the electrochemicalproperties of the core porphyrinogen. Details are discussedin the article by J. P. Hill et al. on p. 2893ff.

MICROREVIEW Contents

G. Bartoli, M. Bartolacci, A. Giuliani,2867E. Marcantoni,* M. Massaccesi

Diastereoselective Lewis Acid Mediated Re-ductions of α-Alkyl-β-Functionalized CarbonylCompounds

Keywords: Carbonyl compounds / Chelates / Dia-stereoselectivity / Lewis acids / Reduction

Eur. J. Org. Chem. 2005, 2855�2862 www.eurjoc.org © 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 2855

SHORT COMMUNICATIONS

L. D. Field, B. A. Messerle,* S. L. Rumble2881

Iridium(I)-Catalysed Tandem Hydrosilylation-Protodesilylation of Imines

Keywords: Hydrosilylation / Imines / Iridium / Solventeffects / Homogeneous catalysis

M. Yoshimatsu,* M. Kawamoto, K. Gotoh2884

First Lewis Acid Catalyzed Generation andReaction of α-Organylsulfanyl and α-Organyl-selanyl Carbenium Ions Using Ethyl α-Fluoro-acetate Derivatives

Keywords: C�C coupling / Carbocations / Scandium /Catalysis / Lewis acids / Fluorinated com-pounds

G. Zoppellaro,* M. Baumgarten2888

One-Step Synthesis of Symmetrically Substi-tuted 2,6-Bis(pyrazol-1-yl)pyridine Systems

Keywords: Nitrogen heterocycles / Halogenation /Grignard reaction / Synthesis design

FULL PAPERS

J. P. Hill,* W. Schmitt, A. L. McCarty,2893K. Ariga, F. D’Souza*

Structures, Spectral and Electrochemical Pro-perties of N-(Naphth-2-ylmethyl)-AppendedPorphyrinogens

Keywords: Porphyrinogen / Redox chemistry /Spectroelectrochemistry / Puckered macro-cycles / Quinones

P. Dıaz Perez, M. I. Garcıa-Moreno,2903C. Ortiz Mellet, J. M. Garcıa Fernandez*

Synthesis and Comparative Glycosidase Inhibi-tory Properties of Reducing CastanospermineAnalogues

Keywords: Carbamates / Castanospermine / Inhibi-tors / Thiocarbamates / Indolizidines /Enzymes

2856 © 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim www.eurjoc.org Eur. J. Org. Chem. 2005, 2855�2862

J. O. Subbotina,* W. M. F. Fabian,*2914E. V. Tarasov, N. N. Volkova, V. A. Bakulev

Synthetic and Theoretical Aspects of NewDimroth Rearrangement of 6-Aminopyran-2-ones to 6-Hydroxypyridin-2-ones via Carb-amoyl Ketenes

Keywords: Rearrangement / Reaction mechanisms /Hydrogen bond / Ketene intermediates /DFT calculations

L. A. Wozniak, M. Gora,2924M. Bukowiecka-Matusiak, S. Mourgues,G. Pratviel, B. Meunier, W. J. Stec*

The P-Stereocontrolled Synthesis of PO/PS-Chimeric Oligonucleotides by Incorporation ofDinucleoside Phosphorothioates Bearing anO-4-Nitrophenyl Phosphorothioate ProtectingGroup

Keywords: Antisense agents / Nucleosides / Oligo-nucleotides / Stereochemistry

H. Abe, M. Takase, Y. Doi, S. Matsumoto,2931M. Furusyo, M. Inouye*

Tautomeric Self-Dimerization and MolecularRecognition Properties of 2-AminopyrimidinoneDerivatives as Triple Hydrogen-Bonding Mod-ules in Molecular Assemblies

Keywords: Molecular recognition / Self-assembly / Nu-cleobases / Hydrogen bonds / Tautomerism

B. M. P. Verbist, W. M. De Borggraeve,*2941S. Toppet, F. Compernolle, G. J. Hoornaert

Development of New Amino(oxo)piperidine-carboxylate Scaffolds and Their Evaluation asβ-Turn Mimics

Keywords: Intramolecular Diels�Alder reaction /2(1H)-pyrazinones / β-Turn mimic


A. S. Abreu, P. M. T. Ferreira,2951M.-J. R. P. Queiroz,* I. C. F. R. Ferreira,R. C. Calhelha, L. M. Estevinho

Synthesis of β-Benzo[b]thienyldehydrophenyl-alanine Derivatives by One-Pot Palladium-Cata-lyzed Borylation and Suzuki Coupling (BSC)and Metal-Assisted Intramolecular Cyclization� Studies of Fluorescence and AntimicrobialActivity

Keywords: Dehydrophenylalanines / Benzothiophenes /Borylation / Suzuki coupling / Cyclization /Indoles / Fluorescence / Antimicrobialactivity

K. Marino, C. Marino, C. Lima, L. Baldoni,2958R. M. de Lederkremer*

The First Chemical Synthesis of UDP[6-3H]-α-D-galactofuranose

Keywords: Carbohydrates / Galactofuranosyltrans-ferase / Isotopic labeling / Nucleotides /UDP-Galf

S. A. A. El Bialy, H. Braun, L. F. Tietze*2965

Enantioselective Synthesis of α-Alkylmalates asthe Pharmacophoric Group of Several NaturalAlkaloids and Glycosides

Keywords: Alkaloids / Antitumor agents / Dioxolan-ones / Enantioselective synthesis / Furans /Glycosides / Malates

D. G. A. Pinto, A. M. S. Silva,* C. M. Brito,2973A. Sandulache, J. R. Carrillo, P. Prieto,A. Dıaz-Ortiz, A. de la Hoz,*J. A. S. Cavaleiro

Reactivity of 3-Styrylchromones as Dienes inDiels�Alder Reactions under MicrowaveIrradiation: A New Synthesis of Xanthones

Keywords: 3-Styrylchromones / Microwave irradia-tion / Xanthone-type compounds / Cyclo-addition / Solvent-free reactions / Abinitio calculations


M. C. Schopohl, A. Faust, D. Mirk,2987R. Fröhlich, O. Kataeva, S. R. Waldvogel*

Synthesis of Rigid Receptors Based on Triphen-ylene Ketals

Keywords: Receptors / Supramolecular chemistry /Synthetic methods / Oxidative couplingreaction / Triphenylene ketals

M. Schelper, O. Buisine, S. Kozhushkov,3000C. Aubert*, A. de Meijere,* M. Malacria*

Cobalt(I)-Mediated Intramolecular [2�2�2]Cocyclizations of (Methylenecyclopropyl)diynesas an Easy Access to Cyclopropanated Oligo-cycles

Keywords: Cyclopropanes / Enediynes / Cobalt / Cycli-zation / Metal template synthesis

M. Kordes, M. Brands, M. Es-Sayed,3008A. de Meijere*

Preparation of Cyclopropane Analogues of theNatural Antibiotic TAN 1057 A/B

Keywords: Amino acids / Antibiotics / Cyclopro-panation

J. Reuber, R. Fröhlich, D. Hoppe*3017

Asymmetric γ-Deprotonation and SubstitutionReactions of (Z)-1,3-Diphenyl-1-propenyl N,N-Diisopropylcarbamate

Keywords: Asymmetric synthesis / Carbanions / Allyliccompounds / Homoaldol addition / (�)-Sparteine

M. Hocek,* R. Pohl, I. Cısarova3026

Highly Methylated Purines and Purinium Saltsas Analogues of Heteromines

Keywords: Purines / Natural products / Cross-coupling / Alkylation / 15N NMR spec-troscopy


A. Isidro-Llobet, J. Guasch-Camell,3031M. Alvarez, F. Albericio*

p-Nitrobenzyloxycarbonyl (pNZ) as a Tempor-ary Nα-Protecting Group in Orthogonal Solid-Phase Peptide Synthesis � Avoiding Diketo-piperazine and Aspartimide Formation

Keywords: Amino protecting group / Nitro reduction /SnCl2 reduction / PNZ group in SPPS /Combinatorial chemistry / Side reactions

G. A. Kraus,* N. Zhang, J. Q. Wei,3040J. H. Jensen*

Regiochemical Control by Remote Substituents� A Selective Synthesis of Angularly FusedRing Systems

Keywords: Diels�Alder / Quinones / Regiocontrol /Regioselectivity

M. Alvaro, C. Aprile, H. Garcıa,* E. Peris3045

A Soluble and Reusable Colorimetric SensorBased on the Covalent Attachment of a Triaryl-pentenedione to Poly(ethylene glycol)

Keywords: Sensors / Polymers / Heterocycles / Cycliza-tion / Colorimetry

P. Astolfi,* M. Panagiotaki, L. Greci3052

New Insights into the Reactivity of Nitrogen Di-oxide with Substituted Phenols: A Solvent Effect

Keywords: Substituted phenols / Nitrogen dioxide /Hydrogen transfer / Electron transfer /Solvent effects

D. Biondini, L. Brinchi, R. Germani,3060L. Goracci, G. Savelli*

Dehydrogenation of Amines to Nitriles inAqueous Micelles

Keywords: Amines / Oxidation / Nickel / Nitrile /Micelles


P. A. Troshin,* A. S. Peregudov,3064D. Mühlbacher, R. N. Lyubovskaya

An Efficient [2�3] Cycloaddition Approach tothe Synthesis of Pyridyl-Appended FullereneLigands

Keywords: Azomethine ylides / Cycloaddition /Fullerenes / N ligands / Picolylamines

A. Pastor,* W. Adam, T. Wirth, G. Toth3075

Diastereoselective Reactions of the Tiglic AcidFunctionality Mediated by Oxazolidine ChiralAuxiliaries: A Mechanistic Comparison ofDMD and m-CPBA Epoxidations versus SingletOxygen and PTAD Ene Reactions

Keywords: Ene reaction / Epoxidation / Hydrogenbonding / Singlet oxygen / Stereochemistry

M. Roussel, T. Benvegnu,* V. Lognone,3085H. Le Deit, I. Soutrel, I. Laurent,D. Plusquellec

Synthesis and Physico-Chemical Properties ofNovel Biocompatible Alkyl d-Mannopyranosid-uronate Surfactants Derived from Alginate

Keywords: Alginate / Bioorganic chemistry / Mann-uronic acid / Micelles / Surfactants

P. Kirsch,* A. Hahn3095

Liquid Crystals Based on Hypervalent SulfurFluorides: Exploring the Steric Effects of ortho-Fluorine Substituents

Keywords: Density functional calculations / Fluorin-ation / Liquid crystals / Hypervalent sulfurfluorides / Mesogens / Molecular modelling

M. A. L. Podeschwa, O. Plettenburg,3101H.-J. Altenbach*

Flexible Stereo- and Regioselective Synthesis ofmyo-Inositol Phosphates (Part 1): Via Symmetri-cal Conduritol B Derivatives

Keywords: Asymmetric synthesis / Biocatalytic resolu-tion / Inositol phosphates / Natural prod-ucts / Phosphorylation / Protecting groups


M. A. L. Podeschwa, O. Plettenburg,3116H.-J. Altenbach*

Flexible Stereo- and Regioselective Synthesis ofmyo-Inositol Phosphates (Part 2): Via Nonsym-metrical Conduritol B Derivatives

Keywords: Asymmetric synthesis / Biocatalytic resolu-tion / Inositol phosphates / Natural prod-ucts / Phosphorylation / Protecting groups

G. L. Sommen, A. Linden, H. Heimgartner*3128

Selenium-Containing Heterocycles From Iso-selenocyanates: Synthesis of 1,3-Selenazolidineand Perhydro-1,3-selenazine Derivatives

Keywords: Cyclizations / Isoselenocyanates / Seleniumheterocycles / Sulfur heterocycles / X-raycrystallography
