Synthesis and ring openings of cinnamate-derived N-unfunctionalised aziridines

• Alan Armstrong and
• Alexandra Ferguson

Beilstein J. Org. Chem. 2012, 8, 1747–1752, doi:10.3762/bjoc.8.199

• Substrate scope of enoate aziridination. Supporting Information Supporting Information File 318: Experimental procedures and characterisation data for all new NH-aziridines, including 1H and 13C NMR spectra for all new compounds. Acknowledgements We thank the EPSRC for their support of this work.

Carbohydrate-auxiliary assisted preparation of enantiopure 1,2-oxazine derivatives and aminopolyols

• Marcin Jasiński,
• Dieter Lentz and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2012, 8, 662–674, doi:10.3762/bjoc.8.74

• MeOH, 40 °C, 3.5 h; (b) DOWEX-50, EtOH, 50 °C, 4 d; (c) BBr3 (3 equiv), CH2Cl2, −78 °C (1 h) then rt, overnight. Supporting Information Supporting Information File 127: Experimental procedures and characterisation data. Supporting Information File 128: 1H NMR and 13C NMR spectra of synthesised

Regio- and stereoselective oxidation of unactivated C–H bonds with Rhodococcus rhodochrous

• Elaine O’Reilly,
• Suzanne J. Aitken,
• Gideon Grogan,
• Paul P. Kelly,
• Nicholas J. Turner and
• Sabine L. Flitsch

Beilstein J. Org. Chem. 2012, 8, 496–500, doi:10.3762/bjoc.8.56

• . Regioselective hydroxylation following incubation of THF ether derivatives with Rhodococcus rhodochrous; *see discussion. Supporting Information Supporting Information File 84: Experimental procedures and characterisation data of synthesised, previously unknown compounds. Acknowledgements We are grateful to

Intramolecular carbenoid ylide forming reactions of 2-diazo-3-keto-4-phthalimidocarboxylic esters derived from methionine and cysteine

• Marc Enßle,
• Stefan Buck,
• Roland Werz and
• Gerhard Maas

Beilstein J. Org. Chem. 2012, 8, 433–440, doi:10.3762/bjoc.8.49

• ylide 12a (DMSO-d6, 400.13 MHz). Supporting Information The supporting information contains experimental procedures and characterisation details for the synthesised compounds. Supporting Information File 110: Experimental part. Acknowledgements We thank Dr. Ulrich Jäger and Professor Willi Kantlehner

Liquid-crystalline nanoparticles: Hybrid design and mesophase structures

• Gareth L. Nealon,
• Romain Greget,
• Cristina Dominguez,
• Zsuzsanna T. Nagy,
• Daniel Guillon,
• Jean-Louis Gallani and
• Bertrand Donnio

Beilstein J. Org. Chem. 2012, 8, 349–370, doi:10.3762/bjoc.8.39

• tetragonal), and the so-called banana phases formed by bent-core mesogens [30][34][35]. This review will focus on publications that describe the preparation and characterisation of discrete thermotropic liquid-crystalline nanoparticle hybrids. Thus topics such as micellar [36] or lyotropic NPs [37][38

On the control of secondary carbanion structure utilising ligand effects during directed metallation

• Andrew E. H. Wheatley,
• Jonathan Clayden,
• Ian H. Hillier,
• Alison Campbell Smith,
• Mark A. Vincent,
• Laurence J. Taylor and
• Joanna Haywood

Beilstein J. Org. Chem. 2012, 8, 50–60, doi:10.3762/bjoc.8.5

• . Attempts to utilise THF in this last system resulted, instead, in the isolation and characterisation of ortho metallated 3-Lio·THF, the solid-state structure of which revealed a dimeric structure analogous to those seen for 1-Lio·THF and 2-Lio·THF [21]. It was subsequently established that the conversion

Sexithiophenes as efficient luminescence quenchers of quantum dots

• Christopher R. Mason,
• Yang Li,
• Paul O’Brien,
• Neil J. Findlay and
• Peter J. Skabara

Beilstein J. Org. Chem. 2011, 7, 1722–1731, doi:10.3762/bjoc.7.202

• LEDs and photovoltaic cells [19][20][21][22][23]. Previously, we reported the synthesis and characterisation of CdS quantum dots in polystyrene beads, in which beads ranging in size from 100 nm to 500 μm were prepared and confocal microscopy showed an even distribution of CdS throughout the polymer

• ). Characterisation of physical properties A film of methyl-capped dimethylaminosexithiophene 1b on ITO glass was obtained by spin coating from a chloroform solution, and the redox properties were compared to those of nonfunctionalised analogue 2b (Figure 2; Table 1). In the positive scan, the cyclic voltammogram for

Chimeric self-sufficient P450cam-RhFRed biocatalysts with broad substrate scope

• Aélig Robin,
• Valentin Köhler,
• Alison Jones,
• Afruja Ali,
• Paul P. Kelly,
• Elaine O'Reilly,
• Nicholas J. Turner and
• Sabine L. Flitsch

Beilstein J. Org. Chem. 2011, 7, 1494–1498, doi:10.3762/bjoc.7.173

• ), after 24 h, of substrates 1, 3, 5, and, after 48 h, of substrates 7, 11, 13 and 15 with P450cam-RhFRed mutants in 48-well plate biotransformations. Supporting Information The Supporting Information features the full experimental procedures, characterisation of the synthesised, previously unknown

The cross-metathesis of methyl oleate with cis-2-butene-1,4-diyl diacetate and the influence of protecting groups

• Arno Behr and
• Jessica Pérez Gomes

Beilstein J. Org. Chem. 2011, 7, 1–8, doi:10.3762/bjoc.7.1

• characterised by NMR spectroscopy. Characterisation of the substrates Methyl oleate (1) 1H NMR (400 MHz; CDCl3): δ (ppm) = 0.88 (t, 3H, J = 8.0 Hz, -CH3), 1.28 (m, 20H, -CH2-), 1.61 (m, 2H, -C(O)-CH2-CH2-), 2.00 (m, 4H, -CH2-CH=), 2.30 (t, 2H, J = 8.0 Hz, -C(O)-CH2-), 3.66 (s, 3H, -CH3), 5.34 (m, 2H, -CH=CH

Cross-metathesis of allylcarboranes with O-allylcyclodextrins

• Ivan Šnajdr,
• Zbyněk Janoušek,
• Jindřich Jindřich and
• Martin Kotora

Beilstein J. Org. Chem. 2010, 6, 1099–1105, doi:10.3762/bjoc.6.126

• prepared carborane-cyclodextrin conjugates 3. Supporting Information Supporting Information File 164: Experimental details and characterisation data of peracetylated cyclodextrins 2a, 2b and 2c. Acknowledgements This work was supported by the Ministry of Education, Youth, and Sports (project No

Halide exchanged Hoveyda-type complexes in olefin metathesis

• Julia Wappel,
• César A. Urbina-Blanco,
• Mudassar Abbas,
• Jörg H. Albering,
• Robert Saf,
• Steven P. Nolan and
• Christian Slugovc

Beilstein J. Org. Chem. 2010, 6, 1091–1098, doi:10.3762/bjoc.6.125

• these compounds in ring opening metathesis polymerisation (ROMP) [21] was also studied. Results and Discussion Synthesis and characterisation Although complex 1 is commercially available, we prepared 1 from (H2IMes)(PCy3)Cl2Ru(3-phenyl-indenylid-1-ene) (M2) as the ruthenium-containing starting material

• field desorption mass spectrometry (FD-MS) measurements. FD-MS was found to be a suitable technique for the characterisation of this type of complex. Selecting appropriate acquisition parameters – the emitter current was slowly increased until desorption/ionisation started, in this way only molecular

Gelation or molecular recognition; is the bis-(α,β-dihydroxy ester)s motif an omnigelator?

• Peter C. Griffiths,
• David W. Knight,
• Ian R. Morgan,
• Amy Ford,
• James Brown,
• Ben Davies,
• Richard K. Heenan,
• Stephen M. King,
• Robert M. Dalgliesh,
• John Tomkinson,
• Stuart Prescott,
• Ralf Schweins and
• Alison Paul

Beilstein J. Org. Chem. 2010, 6, 1079–1088, doi:10.3762/bjoc.6.123

• based on hydrogen bonding of the end-group was confirmed by IR and circular dichroism (CD) spectroscopic characterisation. The specific stereochemistry of the gelator end-groups is a crucial factor, providing an obvious analogy to molecular recognition phenomena. Small-angle neutron scattering provided

Catalysis: transition-state molecular recognition?

• Ian H. Williams

Beilstein J. Org. Chem. 2010, 6, 1026–1034, doi:10.3762/bjoc.6.117

• treatment [6]: “A complete understanding of enzyme catalysis … resolves into a characterisation of two binding processes: that for the transition state, which yields a model for catalysis, and that for the reactant state, which yields a model for … inhibitory effects … The differential stabilisation of the

Design and synthesis of a cyclitol-derived scaffold with axial pyridyl appendages and its encapsulation of the silver(I) cation

• Pierre-Marc Léo,
• Christophe Morin and
• Christian Philouze

Beilstein J. Org. Chem. 2010, 6, 1022–1024, doi:10.3762/bjoc.6.115

• : Synthesis and characterisation data for compounds 1–9 and 1·Ag(I). Acknowledgements The help of Corinne Bailly (CDC-Cambridge database searching), Catherine Belle (spectrophotometry), Béatrice Gennaro (low-temperature NMR experiments) and Guy Serratrice (spectrophotometry) is gratefully acknowledged.

Structure and reactivity in neutral organic electron donors derived from 4-dimethylaminopyridine

• Jean Garnier,
• Alan R. Kennedy,
• Leonard E. A. Berlouis,
• Andrew T. Turner and
• John A. Murphy

Beilstein J. Org. Chem. 2010, 6, No. 73, doi:10.3762/bjoc.6.73

• Information Supporting Information features detailed information on experimental procedures and compound characterisation. Supporting Information File 114: Experimental Part Acknowledgements We thank EPSRC, University of Strathclyde and AstraZeneca for funding and EPSRC Mass Spectrometry Centre, Swansea for

Prins fluorination cyclisations: Preparation of 4-fluoro-pyran and -piperidine heterocycles

• Guillaume G. Launay,
• Alexandra M. Z. Slawin and
• David O'Hagan

Beilstein J. Org. Chem. 2010, 6, No. 41, doi:10.3762/bjoc.6.41

• mixture. aza-Prins reaction under microwave conditions. Reaction conditions: amine 13 (1 equiv), aldehyde (1 equiv), BF3·OEt2, microwave 100 W, 50 °C, 30 min. Supporting Information Supporting Information File 60: Experimental and characterisation details of synthesised compounds. Acknowledgements We

Fused bicyclic piperidines and dihydropyridines by dearomatising cyclisation of the enolates of nicotinyl-substituted esters and ketones

• Heloise Brice,
• Jonathan Clayden and
• Stuart D. Hamilton

Beilstein J. Org. Chem. 2010, 6, No. 22, doi:10.3762/bjoc.6.22

• characterisation data of starting materials Acknowledgements We are grateful to the EPSRC, GlaxoSmithKline (HB) and AstraZeneca (SH) for studentships, and to Drs Emma Blaney and Rukhsana Mohammed for valuable discussions.

Synthesis of lipophilic 1-deoxygalactonojirimycin derivatives as D-galactosidase inhibitors

• Georg Schitter,
• Elisabeth Scheucher,
• Andreas J. Steiner,
• Arnold E. Stütz,
• Martin Thonhofer,
• Chris A. Tarling,
• Stephen G. Withers,
• Jacqueline Wicki,
• Katrin Fantur,
• Eduard Paschke,
• Don J. Mahuran,
• Brigitte A. Rigat,
• Michael Tropak and
• Tanja M. Wrodnigg

Beilstein J. Org. Chem. 2010, 6, No. 21, doi:10.3762/bjoc.6.21

• -glycosidases from Agrobacterium sp. (β-glu/gal Abg), E. coli (β-gal E. coli) as well as with the α-galactosidase from green coffee beans (α-gal GCB). Supporting Information Supporting Information File 4: Full experimental details and characterisation data Acknowledgements G. S. thanks the Institute of

Self-association of an indole based guanidinium-carboxylate-zwitterion: formation of stable dimers in solution and the solid state

• Carolin Rether,
• Wilhelm Sicking,
• Roland Boese and
• Carsten Schmuck

Beilstein J. Org. Chem. 2010, 6, No. 3, doi:10.3762/bjoc.6.3

• HCl in a yield of 84% as a light brown crystalline solid. For the spectroscopic characterisation and as a reference compound also the picrate salt of 2 was prepared by treating a methanolic solution of 2 with picric acid (Scheme 2). The picrate salt 2·H+ was isolated in form of a yellow, crystalline

Diastereoselective functionalisation of benzo-annulated bicyclic sultams: Application for the synthesis of cis-2,4-diarylpyrrolidines

• Susan Kelleher,
• Pierre-Yves Quesne and
• Paul Evans

Beilstein J. Org. Chem. 2009, 5, No. 69, doi:10.3762/bjoc.5.69

• conditions (lithium in liquid ammonia at −78 °C) gave the products of reduction which were converted into the corresponding tosyl derivatives to aid characterisation and purification (Scheme 9). The successful double reduction of compounds 31–33 was observed in moderate/low yields. In the case of compound 31

Three step synthesis of single diastereoisomers of the vicinal trifluoro motif

• Vincent A. Brunet,
• Alexandra M. Z. Slawin and
• David O'Hagan

Beilstein J. Org. Chem. 2009, 5, No. 61, doi:10.3762/bjoc.5.61

• with 3HF∙Et3N and synthesis of the all-syn vicinal trifluoro tosylate 17a. Reaction of α,β-epoxy alcohol 7a and 7b under various fluorination conditions. Ratios determined by 19F NMR. Supporting Information Supporting Information File 80: Experimental methods and full characterisation and spectral

2-Phenyl- tetrahydropyrimidine- 4(1H)-ones – cyclic benzaldehyde aminals as precursors for functionalised β²-amino acids

• Markus Nahrwold,
• Arvydas Stončius,
• Anna Penner,
• Beate Neumann,
• Hans-Georg Stammler and
• Norbert Sewald

Beilstein J. Org. Chem. 2009, 5, No. 43, doi:10.3762/bjoc.5.43

• → rt, 5 h, then aq. Na2SO3, 20 min; b) H2, 10% Pd/C, MeOH, rt, 16 h; c) FmocOSu, NaHCO3, acetone/H2O, rt, 4 h. Supporting Information Supporting Information File 72: Detailed synthetic procedures and characterisation data for all new compounds reported in this paper. Acknowledgements The authors

From discovery to production: Scale- out of continuous flow meso reactors

• Peter Styring and
• Ana I. R. Parracho

Beilstein J. Org. Chem. 2009, 5, No. 29, doi:10.3762/bjoc.5.29

• activating agents such as substituted phosphines, or else catalysts possessing ligands with complex and expensive motifs [1]. Often, the scale at which such reactions are performed is far greater than that required for initial characterisation and property screening [2][3]. Once a compound is identified for

Asymmetric synthesis of biaryl atropisomers by dynamic resolution on condensation of biaryl aldehydes with (−)-ephedrine or a proline- derived diamine

• Ann Bracegirdle,
• Jonathan Clayden and
• Lai Wah Lai

Beilstein J. Org. Chem. 2008, 4, No. 47, doi:10.3762/bjoc.4.47

• characterisation data, of the remaining compounds reported in this paper. Supporting Information File 106: Full experimental data for all new compounds reported in the paper. Acknowledgements We are grateful to GlaxoSmithKline and to the EPSRC for studentships (to AB and LWL).

C₂-symmetric bisamidines: Chiral Brønsted bases catalysing the Diels- Alder reaction of anthrones

• Deniz Akalay,
• Gerd Dürner,
• Jan W. Bats and
• Michael W. Göbel

Beilstein J. Org. Chem. 2008, 4, No. 28, doi:10.3762/bjoc.4.28

• . Influence of the solvent on the bisamidine catalyzed Diels-Alder reaction. Influence of temperature on the Diels-Alder reaction. Scope of the Diels-Alder-reaction. Supporting Information Supporting Information File 4: Supporting information features characterisation data and copies of 1H- and 13C-NMR