Aggregation behavior of amphiphilic cyclodextrins in a nonpolar solvent: evidence of large-scale structures by atomistic molecular dynamics simulations and solution studies

• Giuseppina Raffaini,
• Fabio Ganazzoli and
• Antonino Mazzaglia

Beilstein J. Org. Chem. 2016, 12, 73–80, doi:10.3762/bjoc.12.8

• ), could be utilized in perspective in a future investigation on similar aCD with n > 0. In the following, we discuss our simulation and experimental results in the order, and then the simulation methodology and the dynamic light scattering procedure in the Experimental section. Results and Discussion

Supramolecular polymer assembly in aqueous solution arising from cyclodextrin host–guest complexation

• Jie Wang,
• Zhiqiang Qiu,
• Yiming Wang,
• Li Li,
• Xuhong Guo,
• Duc-Truc Pham,
• Stephen F. Lincoln and
• Robert K. Prud’homme

Beilstein J. Org. Chem. 2016, 12, 50–72, doi:10.3762/bjoc.12.7

• [112][113][114]. Conclusion and Perspective In this brief review it is shown that there is a plethora of routes to supramolecular polymer networks in aqueous solution based on cyclodextrin host–guest complexation. Through variations in this supramolecular chemistry at the molecular level macroscopic

Effective immobilisation of a metathesis catalyst bearing an ammonium-tagged NHC ligand on various solid supports

• Krzysztof Skowerski,
• Jacek Białecki,
• Stefan J. Czarnocki,
• Karolina Żukowska and
• Karol Grela

Beilstein J. Org. Chem. 2016, 12, 5–15, doi:10.3762/bjoc.12.2

• endeavour aimed at getting a broader perspective. Immobilisation of 8 on iron powder First, we attempted to prepare a model for a magnetically separable catalyst [55]. This idea has been explored previously by attaching tagged Ru complexes to specially designed magnetically active nanoparticles. We wondered

Learning from the unexpected in life and DNA self-assembly

• Jennifer M. Heemstra

Beilstein J. Org. Chem. 2015, 11, 2713–2720, doi:10.3762/bjoc.11.292

• these experiences as hindering our progress, they should be embraced and appreciated for their ability to lead to new discoveries. In this perspective, I will discuss the unexpected events that have shaped my career path and the early stages of my independent research program. Keywords: aptamers; DNA

• early career, it is clear that gender and work-life balance issues have in many ways shaped the path that I have taken. I have expressed my perspective on some of these issues in depth elsewhere [1], and thus will only mention the topic briefly here. The data show that there is significant progress that

• insights are often the key to making a project successful, and sometimes even inspire the design a new project, but they can tend to get lost among all of the data in a manuscript, or relegated to the supporting information. Thus, in this perspective article, I am excited to have the opportunity to

Smart molecules for imaging, sensing and health (SMITH)

• Bradley D. Smith

Beilstein J. Org. Chem. 2015, 11, 2540–2548, doi:10.3762/bjoc.11.274

• imaging, ion-pair receptors, rotaxane synthesis, squaraine rotaxanes, and synthtavidin technology. The article concludes with a short perspective of likely future directions in biomedical supramolecular chemistry. Keywords: fluorescence; ion-pair receptors; membrane transport; molecular imaging; rotaxane

Life lessons

• Jonathan R. Nitschke

Beilstein J. Org. Chem. 2015, 11, 2350–2354, doi:10.3762/bjoc.11.256

• perspective, the underlying attitude served me well. I loved the environment at Berkeley – the place was fizzing with intellectual energy, manifested both as world-class scholarship and as Hunter S. Thompson-style craziness. Under T. Don Tilley’s supervision, my Ph.D. work involved the development of

Cu(I)-catalyzed N,N’-diarylation of natural diamines and polyamines with aryl iodides

• Svetlana P. Panchenko,
• Alexei D. Averin,
• Maksim V. Anokhin,
• Olga A. Maloshitskaya and
• Irina P. Beletskaya

Beilstein J. Org. Chem. 2015, 11, 2297–2305, doi:10.3762/bjoc.11.250

• polyamines using aryl iodides with electron-donating and electron-withdrawing substituents in order to identify conditions for the synthesis of a wide range of perspective derivatives of these di- and polyamines. Results and Discussion N,N’-Diarylation of diamines The investigated diamines 1–4, triamines 5

Ru complexes of Hoveyda–Grubbs type immobilized on lamellar zeolites: activity in olefin metathesis reactions

• Hynek Balcar,
• Naděžda Žilková,
• Martin Kubů,
• Michal Mazur,
• Zdeněk Bastl and
• Jiří Čejka

Beilstein J. Org. Chem. 2015, 11, 2087–2096, doi:10.3762/bjoc.11.225

• with sterically enlarged NHC ligand supported on SBA-15 exhibited high stability and was effective in flow reactions [22]. According to our knowledge, zeolites have not been considered as perspective supports for the immobilization of Ru metathesis catalysts due to small diameters of their pores (<1 nm

New aryloxybenzylidene ruthenium chelates – synthesis, reactivity and catalytic performance in ROMP

• Patrycja Żak,
• Szymon Rogalski,
• Mariusz Majchrzak,
• Maciej Kubicki and
• Cezary Pietraszuk

Beilstein J. Org. Chem. 2015, 11, 1910–1916, doi:10.3762/bjoc.11.206

• catalyst is presented. ROMP of monomer 15. Conditions: CDCl3, 40 °C, 0.08 M, [15]:[Ru] = 200. ROMP of monomer 15. Conditions: CDCl3, 23 °C, 0.08 M, [15]:[Ru] = 200. A perspective view of complex 16, the ellipsoids are drawn at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary

The synthesis of active pharmaceutical ingredients (APIs) using continuous flow chemistry

• Marcus Baumann and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2015, 11, 1194–1219, doi:10.3762/bjoc.11.134

• in addition to the equipment. From an academic perspective this is a positive and beneficial contribution to the progression of the subject, however, this can significantly restrict the translational value of the methodology with respect to adoption or convenient uptake by industry. Commonly industry

• the reactor should be made here from a scale-up perspective as this was not explored in the paper. Overall, this small scale syringe pump based set-up enabled the preparation of rufinamide (95) within ~11 minutes processing time and with a productivity of ~0.22 g/h, although this does not take into

An intramolecular C–N cross-coupling of β-enaminones: a simple and efficient way to precursors of some alkaloids of Galipea officinalis

• Hana Doušová,
• Radim Horák,
• Zdeňka Růžičková and
• Petr Šimůnek

Beilstein J. Org. Chem. 2015, 11, 884–892, doi:10.3762/bjoc.11.99

• molecules from a C–N cross-coupling perspective. There are relatively few works (about ten) dealing with these very useful molecules [35][36][37][38][39][40][41][42][43][44][45][46], in comparison to the hundreds of papers dedicated to the other substrates. Due to their electronic nature, β-enaminones can

Hydrogenation of unactivated enamines to tertiary amines: rhodium complexes of fluorinated phosphines give marked improvements in catalytic activity

• Sergey Tin,
• Tamara Fanjul and
• Matthew L. Clarke

Beilstein J. Org. Chem. 2015, 11, 622–627, doi:10.3762/bjoc.11.70

• require quite different ligands to those needed for enamide hydrogenation. From a synthetic perspective, large scale reduction processes generally prefer the use of hydrogen gas to any other reductant, since it potentially saves on cost, waste, atom-economy, solvent and water use; the catalysts identified

Chemoselective O-acylation of hydroxyamino acids and amino alcohols under acidic reaction conditions: History, scope and applications

• Tor E. Kristensen

Beilstein J. Org. Chem. 2015, 11, 446–468, doi:10.3762/bjoc.11.51

• for many applications, particularly within the academic sector. Purification by flash column chromatography then easily becomes a practical, standardized procedure. If a longer historical perspective is adopted, dating prior to the advent of widespread flash column chromatography, one will realize

A simple and efficient method for the preparation of 5-hydroxy-3-acyltetramic acids

• Johanna Trenner and
• Evgeny V. Prusov

Beilstein J. Org. Chem. 2015, 11, 323–327, doi:10.3762/bjoc.11.37

• natural products as delaminomycin A [1], embellicin A [2] and integramycin [3] (Figure 1). Additionally, 5-heterosubstituted-3-acyltetramic acids were recently identified by Moloney as perspective lead structures for the development of novel antibacterial compounds [4]. Intrigued by their potential

Natural phenolic metabolites with anti-angiogenic properties – a review from the chemical point of view

• Qiu Sun,
• Jörg Heilmann and
• Burkhard König

Beilstein J. Org. Chem. 2015, 11, 249–264, doi:10.3762/bjoc.11.28

• from preexisting ones. Under physiological conditions, angiogenesis is vital for foetal development, tissue regeneration and wound healing. From a pathophysiologic perspective, massive vascular growth or abnormal shape formation promotes many ailments including cancer, inflammation, and eye illnesses

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

• ) [21][22][23][24] atom (Type II). Most catalysts based on Salen-type ligands are substrate specific and are most efficient for the copolymerisation of CO2 with propylene oxide (PO). The use of zinc-based catalysts of Type I appears more favourable from an environmental perspective compared to the use

First chemoenzymatic stereodivergent synthesis of both enantiomers of promethazine and ethopropazine

• Paweł Borowiecki,
• Daniel Paprocki and
• Maciej Dranka

Beilstein J. Org. Chem. 2014, 10, 3038–3055, doi:10.3762/bjoc.10.322

The unexpected influence of aryl substituents in N-aryl-3-oxobutanamides on the behavior of their multicomponent reactions with 5-amino-3-methylisoxazole and salicylaldehyde

• Volodymyr V. Tkachenko,
• Elena A. Muravyova,
• Sergey M. Desenko,
• Oleg V. Shishkin,
• Svetlana V. Shishkina,
• Dmytro O. Sysoiev,
• Thomas J. J. Müller and
• Valentin A. Chebanov

Beilstein J. Org. Chem. 2014, 10, 3019–3030, doi:10.3762/bjoc.10.320

• spectrum of biological activity [5][6], which led to choose acetoacetamides as perspective methylene-active compounds for further studies of multicomponent reactions. The interactions of 3-oxobutanamides with aldehydes and a number of aminoazoles, namely 3-amino-1,2,4-triazoles [7][8][9][10][11], 5

Modification of physical properties of poly(L-lactic acid) by addition of methyl-β-cyclodextrin

• Toshiyuki Suzuki,
• Ayaka Ei,
• Yoshihisa Takada,
• Hiroki Uehara,
• Takeshi Yamanobe and
• Keiko Takahashi

Beilstein J. Org. Chem. 2014, 10, 2997–3006, doi:10.3762/bjoc.10.318

• superior to MeCD, MeCD is a biobased material and is thus advantageous from an environmental perspective. These TGA results show that MeCD acts as a plasticizer for PLLA, and the fraction of the amorphous phase increases. Since the Tg of the samples may be affected by the MeCD addition, DSC measurements

Scalable synthesis of 5,11-diethynylated indeno[1,2-b]fluorene-6,12-diones and exploration of their solid state packing

• Bradley D. Rose,
• Peter J. Santa Maria,
• Aaron G. Fix,
• Chris L. Vonnegut,
• Lev N. Zakharov,
• Sean R. Parkin and
• Michael M. Haley

Beilstein J. Org. Chem. 2014, 10, 2122–2130, doi:10.3762/bjoc.10.219

• transport these are the orbitals that the extra electron would occupy. The Kohn–Sham LUMO density in Figure 3 is predominately located on the indacene moiety and the oxygen. From this perspective the best candidates for n-channel OFET materials would have large overlap between the indacene moiety and oxygen

Multichromophoric sugar for fluorescence photoswitching

• Stéphane Maisonneuve,
• Rémi Métivier,
• Pei Yu,
• Keitaro Nakatani and
• Juan Xie

Beilstein J. Org. Chem. 2014, 10, 1471–1481, doi:10.3762/bjoc.10.151

• molecule. This is valuable in terms of photon (thus energy) saving, since “switching a few photochromes leads to quenching many fluorophores”. In this perspective, we decided to design a multichromophoric glycopyranoside bearing three DCM fluorophores and one photochromic bis(dithiazole)ethane [14][15][16

Rasta resin–triphenylphosphine oxides and their use as recyclable heterogeneous reagent precursors in halogenation reactions

• Xuanshu Xia and
• Patrick H. Toy

Beilstein J. Org. Chem. 2014, 10, 1397–1405, doi:10.3762/bjoc.10.143

• ; polymer-supported reagent; rasta resin; triphenylphosphine oxide; Introduction One of the major drawbacks of the Wittig [1] and Mitsunobu [2][3] reactions is that they result in the formation of a stoichiometric quantity of triphenylphosphine oxide (1) as a byproduct. From an atom economy perspective

Automated solid-phase peptide synthesis to obtain therapeutic peptides

• Veronika Mäde,
• Sylvia Els-Heindl and
• Annette G. Beck-Sickinger

Beilstein J. Org. Chem. 2014, 10, 1197–1212, doi:10.3762/bjoc.10.118

• significantly smaller in size and hence, easier and cheaper to synthesize using chemical strategies [5]. Thereby, they provide a vast perspective for novel drug design. Table 1 summarizes valuable virtues and pivotal shortcomings of therapeutic peptides compared to traditional small organic molecules. The high

Allenylphosphine oxides as simple scaffolds for phosphinoylindoles and phosphinoylisocoumarins

• G. Gangadhararao,
• Ramesh Kotikalapudi,
• M. Nagarjuna Reddy and
• K. C. Kumara Swamy

Beilstein J. Org. Chem. 2014, 10, 996–1005, doi:10.3762/bjoc.10.99

• ; propargyl alcohols; Introduction Allenes, by virtue of cumulative double bonds that facilitate reactions with diverse classes of substrates, are versatile building blocks from a synthetic perspective [1][2]. They are also found in many natural products, pharmaceuticals [3] and molecular materials [4]. Thus

Molecular architecture with carbohydrate functionalized β-peptides adopting 3₁₄-helical conformation

• Nitin J. Pawar,
• Navdeep S. Sidhu,
• George M. Sheldrick,
• Dilip D. Dhavale and
• Ulf Diederichsen

Beilstein J. Org. Chem. 2014, 10, 948–955, doi:10.3762/bjoc.10.93

• , galactose and xylose derivatives were incorporated as sugar units in rigid peptide templates. Keeping the proper β3-configuration for getting a β-peptide 314-helix (2–6) the isopropylidene protecting group and an anomeric acetal are structurally well tolerated. An additional perspective emerged from the