Anion effect controlling the selectivity in the zinc-catalysed copolymerisation of CO₂ and cyclohexene oxide

• Sait Elmas,
• Muhammad Afzal Subhani,
• Walter Leitner and
• Thomas E. Müller

Beilstein J. Org. Chem. 2015, 11, 42–49, doi:10.3762/bjoc.11.7

• the product selectivity and the activity of the complexes in catalysing the reaction of CO2 with cyclohexene oxide. Results and Discussion Synthesis and characterisation of binuclear [LZn2](X)2 complexes Complexes [LZn2]](CF3SO3)2 (1) and [LZn2](p-TSO3)2 (2) (Scheme 2) were prepared by reacting the

Solution processable diketopyrrolopyrrole (DPP) cored small molecules with BODIPY end groups as novel donors for organic solar cells

• Diego Cortizo-Lacalle,
• Calvyn T. Howells,
• Upendra K. Pandey,
• Joseph Cameron,
• Neil J. Findlay,
• Anto Regis Inigo,
• Tell Tuttle,
• Peter J. Skabara and
• Ifor D. W. Samuel

Beilstein J. Org. Chem. 2014, 10, 2683–2695, doi:10.3762/bjoc.10.283

• with bis-vinylthienyl groups exceeded 4.5% [43]. Although, a few dyads and triads containing both the DPP and BODIPY core have been prepared [44][45][46], here we present the synthesis and characterisation of two novel BODIPY-DPP-BODIPY triads linked by thiophene bridges. These materials were tested in

• experimentally. The good agreement between the computational and experimental results shows that wB97XD/TDDFT can be a useful tool in predicting the absorption of BODIPY-based triads and compounds with multiple absorbing units, which are normally difficult to describe computationally. Device characterisation

• deposition. 20 nm of calcium and 200 nm of aluminium were thermally evaporated at a base pressure of 2 × 10−6 mbar. Devices were then encapsulated with a glass cover slip and a UV curable optical adhesive from Thorlabs. The active area of the devices was 6 mm2. Characterisation was performed in air using a

Cyclodextrin-grafted polymers functionalized with phosphanes: a new tool for aqueous organometallic catalysis

• Jonathan Potier,
• Stéphane Menuel,
• David Mathiron,
• Véronique Bonnet,
• Frédéric Hapiot and
• Eric Monflier

Beilstein J. Org. Chem. 2014, 10, 2642–2648, doi:10.3762/bjoc.10.276

• interface to favour the substrate conversion. Herein, we detailed the synthesis and characterisation of this polymer and its catalytic behaviour in Rh-catalyzed hydroformylation of 1-hexadecene. Results and Discussion A wide range of CD-based polymers have already been described in the literature [13][14

Phosphinocyclodextrins as confining units for catalytic metal centres. Applications to carbon–carbon bond forming reactions

• Matthieu Jouffroy,
• Rafael Gramage-Doria,
• David Sémeril,
• Dominique Armspach,
• Dominique Matt,
• Werner Oberhauser and
• Loïc Toupet

Beilstein J. Org. Chem. 2014, 10, 2388–2405, doi:10.3762/bjoc.10.249

• containing enantiomeric alcohols was analysed by GC with a Chirasil-DEX CB column (25 m × 0.25 mm). HUGPHOS-1, HUGPHOS-2 [38], WIDEPHOS [39], and [PdCl(dmba)]2 [89], were synthesized according to literature procedures. The synthesis and characterisation of compounds 5, 9, 12 and 13, as well as the general

Facile synthesis of 1H-imidazo[1,2-b]pyrazoles via a sequential one-pot synthetic approach

• András Demjén,
• Márió Gyuris,
• János Wölfling,
• László G. Puskás and
• Iván Kanizsai

Beilstein J. Org. Chem. 2014, 10, 2338–2344, doi:10.3762/bjoc.10.243

• -3CRa. Sequential one-pot GBB library generationa. Synthesis of highly substituted 1H-imidazo[1,2-b]pyrazolesa. Supporting Information Supporting Information File 372: Experimental and characterisation data. Acknowledgements This work was supported financially by the New Hungary Development Plan

Molecular recognition of AT-DNA sequences by the induced CD pattern of dibenzotetraaza[14]annulene (DBTAA)–adenine derivatives

• Marijana Radić Stojković,
• Marko Škugor,
• Łukasz Dudek,
• Jarosław Grolik,
• Julita Eilmes and
• Ivo Piantanida

Beilstein J. Org. Chem. 2014, 10, 2175–2185, doi:10.3762/bjoc.10.225

• DNA and RNA sequences. Results and Discussion Synthesis The synthetic routes to the new adenine–DBTAA conjugates AP3am and AP5 are summarized in Scheme 2, the details of which are given in the Experimental section. Spectroscopic characterisation of DBTAA derivatives in aqueous medium Novel compounds

Synthesis and bioactivity of analogues of the marine antibiotic tropodithietic acid

• Patrick Rabe,
• Tim A. Klapschinski,
• Nelson L. Brock,
• Christian A. Citron,
• Paul D’Alvise,
• Lone Gram and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2014, 10, 1796–1801, doi:10.3762/bjoc.10.188

• ). Synthesis of halogenated TDA analogues. Further compounds included in this SAR study. Bioactivity tests with TDA and TDA analogues. Supporting Information Supporting Information File 616: Synthetic procedures, compound characterisation data and copies of NMR spectra. Acknowledgements This work was funded

The search for new amphiphiles: synthesis of a modular, high-throughput library

• George C. Feast,
• Thomas Lepitre,
• Xavier Mulet,
• Charlotte E. Conn,
• Oliver E. Hutt,
• G. Paul Savage and
• Calum J. Drummond

Beilstein J. Org. Chem. 2014, 10, 1578–1588, doi:10.3762/bjoc.10.163

• ]. Increasing the lattice parameter of the liquid-crystalline phase may also facilitate the uptake of larger bioactive molecules [4]. At present, only a small selection of amphiphiles is used in the aforementioned applications. Research into the design, synthesis, and material characterisation of new

• amphiphiles has been underexplored, generally due to technical difficulties in the synthesis and handling of such compounds [13]. Thus, a new method combining high-throughput synthesis and liquid-crystalline phase characterisation may open new territory in the field of amphiphile discovery. Furthermore

• File 416: Experimental procedures, chemical characterisation data (including 13C NMR spectra) and preliminary SAXS analysis. Acknowledgements The authors would like to acknowledge Donald Thomas and Douglas Lawes, of the NMR facility within the Mark Wainwright Analytical Centre at the University of New

4-Hydroxy-6-alkyl-2-pyrones as nucleophilic coupling partners in Mitsunobu reactions and oxa-Michael additions

• Michael J. Burns,
• Thomas O. Ronson,
• Richard J. K. Taylor and
• Ian J. S. Fairlamb

Beilstein J. Org. Chem. 2014, 10, 1159–1165, doi:10.3762/bjoc.10.116

• pyronyl vinyl ethers 7. Supporting Information Supporting Information File 116: Detailed experimental procedures, characterisation data for compounds 3b–e, 4a–l, 5d, 7a–i and 9 and 1H NMR spectra for novel compounds. Acknowledgements T.O.R. is funded by an EPSRC DTA PhD studentship. We are grateful to

Self-assembly of metallosupramolecular rhombi from chiral concave 9,9’-spirobifluorene-derived bis(pyridine) ligands

• Rainer Hovorka,
• Sophie Hytteballe,
• Torsten Piehler,
• Georg Meyer-Eppler,
• Filip Topić,
• Kari Rissanen,
• Marianne Engeser and
• Arne Lützen

Beilstein J. Org. Chem. 2014, 10, 432–441, doi:10.3762/bjoc.10.40

• (C-9), 24.8 (C-17) ppm (* signal assignment might be interchanged); HRMS-ESI (m/z): [M + H]+ calcd for [C37H27N2]+, 499.2169; found, 499.2160. [α]D24 −128.1° (c 0.39, CHCl3). Preparation and characterisation of the metal complexes: Approximately 10 µmol of a ligand and an equimolar amount of [(dppp

Concise, stereodivergent and highly stereoselective synthesis of cis- and trans-2-substituted 3-hydroxypiperidines – development of a phosphite-driven cyclodehydration

• Peter H. Huy,
• Julia C. Westphal and
• Ari M. P. Koskinen

Beilstein J. Org. Chem. 2014, 10, 369–383, doi:10.3762/bjoc.10.35

• Weinreb amides 5. Cyclodehydration of amino alcohols 9a–d to piperidinols 11a–d. Cyclodehydration of amino alcohols and diols 12a–h to heterocycles 13a–h. Diastereoselectivity in the reduction of ketone 14a. Supporting Information Supporting Information File 64: Experimental and characterisation data

Intermediates in monensin biosynthesis: A late step in biosynthesis of the polyether ionophore monensin is crucial for the integrity of cation binding

• Wolfgang Hüttel,
• Jonathan B. Spencer and
• Peter F. Leadlay

Beilstein J. Org. Chem. 2014, 10, 361–368, doi:10.3762/bjoc.10.34

• . Further progress has been hampered by the instability of the various epoxide species as well as by the complexity of the product mixtures, containing both monensin A-related and monensin B-related compounds. Nevertheless, the structural characterisation of one of the products of such blocked mutants as an

• of product in unoptimised 50 mL shake flask cultures, over 100-fold more than the wild type strain. This overproduction greatly facilitated the characterisation of the products of the ΔmonD and ΔmonE mutants. For polyether production the mutant strains were initially cultivated in the SM-16 medium

Tuning the interactions between electron spins in fullerene-based triad systems

• Maria A. Lebedeva,
• Thomas W. Chamberlain,
• E. Stephen Davies,
• Bradley E. Thomas,
• Martin Schröder and
• Andrei N. Khlobystov

Beilstein J. Org. Chem. 2014, 10, 332–343, doi:10.3762/bjoc.10.31

• [22] and was reacted with [60]fulleropyrrolidine 9 to give the benzyl ester protected compound 11 in 68% yield. Subsequent deprotection of 11 by CF3SO3H yielded the insoluble product 12 that precluded characterisation by solution based methods. However, MALDI–MS of 12 showed a molecular ion peak with

• physical properties similar to those of 1–4 and 6. Electrochemical characterisation of fullerene triads 1–6 Compounds 1–6 were studied by cyclic voltammetry (CV) as solutions in o-dichlorobenzene in order to investigate the sequence of electron additions and possible electronic interactions in these triads

• containing C70 the results are less clear where additional electrode processes are observed. However we do not attribute these features to intramolecular fullerene–fullerene interactions. EPR spectroscopic characterisation of the fullerene triads in the reduced state The electron spin–spin interactions that

Synthesis of the B-seco limonoid core scaffold

• Hanna Bruss,
• Hannah Schuster,
• Rémi Martinez,
• Markus Kaiser,
• Andrey P. Antonchick and
• Herbert Waldmann

Beilstein J. Org. Chem. 2014, 10, 194–208, doi:10.3762/bjoc.10.15

• Supporting Information File 220: Experimental procedures and characterisation data. Acknowledgements This research was supported by the European Research Council (ERC European Advanced Investigator Grant to H.W.), the Max Planck Society and the Fonds der Chemischen Industrie (Kekulé-stipend to H.S.).

Multigramme synthesis and asymmetric dihydroxylation of a 4-fluorobut-2E-enoate

• James A. B. Laurenson,
• John A. Parkinson,
• Jonathan M. Percy,
• Giuseppe Rinaudo and
• Ricard Roig

Beilstein J. Org. Chem. 2013, 9, 2660–2668, doi:10.3762/bjoc.9.301

• . Experimental A full range of experimental procedures and characterisation data is presented in Supporting Information File 1. Side product 27 isolated from attempted fluorination. The ligand panel used in the asymmetric dihydroxylation studies. The bold oxygen shows the point of attachment; individual ligands

Gold(I)-catalysed one-pot synthesis of chromans using allylic alcohols and phenols

• Eloi Coutant,
• Paul C. Young,
• Graeme Barker and
• Ai-Lan Lee

Beilstein J. Org. Chem. 2013, 9, 1797–1806, doi:10.3762/bjoc.9.209

• File 270: Full experimental procedures, characterisation for all new compounds and copies of 1H and 13C NMR spectra. Acknowledgements We thank EPSRC (EP/K00736X/1), EPSRC DTA studentship (PCY), Erasmus Programme and Ministère français de l'Éducation Nationale (EC) for funding. Mass spectrometry data

Synthesis of the reported structure of piperazirum using a nitro-Mannich reaction as the key stereochemical determining step

• James C. Anderson,
• Andreas S. Kalogirou,
• Michael J. Porter and
• Graham J. Tizzard

Beilstein J. Org. Chem. 2013, 9, 1737–1744, doi:10.3762/bjoc.9.200

• . Comparison of selected 13C NMR chemical shifts of piperazirum, 2 and 2·HCl. Supporting Information Supporting Information File 268: Further experimental and characterisation data. Acknowledgements We thank the Cyprus State Scholarship Foundation for funding, Dr. L. Haigh and Mr. J. Hill for providing mass

Development of an additive-controlled, SmI₂-mediated stereoselective sequence: Telescoped spirocyclisation, lactone reduction and Peterson elimination

• Brice Sautier,
• Karl D. Collins and
• David J. Procter

Beilstein J. Org. Chem. 2013, 9, 1443–1447, doi:10.3762/bjoc.9.163

• stereoselective spirocyclisation/lactone reduction. Telescoped stereoselective spirocyclisation/lactone reduction/Peterson elimination. Optimisation of SmI2–mediated spirocyclisation conditions. Supporting Information Supporting Information File 376: General experimental procedures and characterisation data

Synthesis of the calcilytic ligand NPS 2143

• Henrik Johansson,
• Thomas Cailly,
• Alex Rojas Bie Thomsen,
• Hans Bräuner-Osborne and
• Daniel Sejer Pedersen

Beilstein J. Org. Chem. 2013, 9, 1383–1387, doi:10.3762/bjoc.9.154

• disclose for the first time a complete experimental description, detailed characterisation and assessment of enantiomeric purity for (R)-3. An efficient, reproducible and scalable synthesis of (R)-3 that requires a minimum of chromatographic purification steps is presented. (R)-3 was obtained in excellent

• that the published [12][13][14] experimental details and characterisation for ligand (R)-3 were unsatisfactory, and we were unable to reproduce several of the reported synthetic procedures. Moreover, we were surprised to discover the lack of assessment of optical purity for (R)-3. Considering that the

• synthesis for racemic and enantiopure calcilytic agent (R)-3, including detailed spectroscopic, chromatographic and pharmacological characterisation. Results and Discussion We decided to synthesise (R)-3 using the same overall strategy published by others employing the three fragments depicted in Scheme 1

Camera-enabled techniques for organic synthesis

• Steven V. Ley,
• Richard J. Ingham,
• Matthew O’Brien and
• Duncan L. Browne

Beilstein J. Org. Chem. 2013, 9, 1051–1072, doi:10.3762/bjoc.9.118

• system in a relevant way (Figure 13). In some cases, highly specialised software is applied for the characterisation of experimental imagery. On an industrial scale, reproducible crystallisation is a crucial method for purification, and many physical parameters for the crystallisation process can be

• captured. The shape distribution of nascent crystals is one such parameter that is most effectively measured visually. For example, a particle characterisation system and associated software developed by Malvern Instruments, Inc. [65][66] is routinely applied to analyse particle sizes (Figure 14a,b). One

Use of 3-[¹⁸F]fluoropropanesulfonyl chloride as a prosthetic agent for the radiolabelling of amines: Investigation of precursor molecules, labelling conditions and enzymatic stability of the corresponding sulfonamides

• Reik Löser,
• Steffen Fischer,
• Achim Hiller,
• Martin Köckerling,
• Uta Funke,
• Aurélie Maisonial,
• Peter Brust and
• Jörg Steinbach

Beilstein J. Org. Chem. 2013, 9, 1002–1011, doi:10.3762/bjoc.9.115

• of the analogous fluoroacetamide. Keywords: fluorine-18; hydrolytic metabolism; prosthetic groups; radiochemistry; sulfonamides; Introduction The importance of molecular imaging, i.e., the characterisation and measurement of biological processes in living organisms at the molecular level using

• fraction of the product related to the total 18F-activity. Supporting Information Supporting Information File 24: Experimental procedures, characterisation data of synthesised compounds and supplementary graphical material. Acknowledgements We would like to thank Dr. Claudia Birkemeyer (University of

Synthesis of skeletally diverse alkaloid-like molecules: exploitation of metathesis substrates assembled from triplets of building blocks

• Sushil K. Maurya,
• Mark Dow,
• Stuart Warriner and
• Adam Nelson

Beilstein J. Org. Chem. 2013, 9, 775–785, doi:10.3762/bjoc.9.88

• and subsequent desulfonylation. Derivatisation and deprotection of final products. Supporting Information Supporting Information File 122: Experimental and compound characterisation. Acknowledgements We thank the European Commission for a Marie Curie International Incoming Fellowship (to S.K.M.) and

Asymmetric Diels–Alder reaction with >C=P– functionality of the 2-phosphaindolizine-η¹-P-aluminium(O-menthoxy) dichloride complex: experimental and theoretical results

• Rajendra K. Jangid,
• Nidhi Sogani,
• Neelima Gupta,
• Raj K. Bansal,
• Moritz von Hopffgarten and
• Gernot Frenking

Beilstein J. Org. Chem. 2013, 9, 392–400, doi:10.3762/bjoc.9.40

• -Phosphaindolizines (Scheme 2) were prepared by the [4 + 1] cyclocondensation method from the reaction of the respective 1-alkyl-2-ethylpyridinium bromide with phosphorus trichloride in the presence of triethylamine, as described in literature [56]. Analysis and characterisation of the products Melting points were

Synthesis and testing of the first azobenzene mannobioside as photoswitchable ligand for the bacterial lectin FimH

• Vijayanand Chandrasekaran,
• Katharina Kolbe,
• Femke Beiroth and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2013, 9, 223–233, doi:10.3762/bjoc.9.26

• , open-gate conformation). Bottom: (Z)-isomer (C, closed-gate; D, open-gate conformation). Synthesis of azobenzene mannoside 6 and azobenzene mannobioside 2 by glycosylation. Characterisation of the (E)- and (Z)-isomers of azobenzene glycosides 6 and 2. Inhibition of adhesion of E. coli to a mannan

Cyclodextrin-based nanosponges as drug carriers

• Francesco Trotta,
• Marco Zanetti and
• Roberta Cavalli

Beilstein J. Org. Chem. 2012, 8, 2091–2099, doi:10.3762/bjoc.8.235

• instance, carboxylated nanosponges can be obtained by reacting pristine carbonate nanosponges with succinic anhydride. Detailed physicochemical characterisation is reported in the literature, demonstrating that carbonate nanosponges are thermally stable up to 300 °C and can therefore be sterilised by