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OBC issue 22: artificial O2 and CO receptors and oxidative Umpolung on the covers

16 May 2012

This colourful front cover is courtesy of Koji Kano and colleagues from Doshisha University. This HOT paper from Kano et al. discusses a study on how to control the circulation time of a synthetic oxygen and carbon monoxide receptor by attaching poly(ethylene glycol) chains to the periphery of an iron porphyrin. By attaching chains of varying molecular weight Kano et al. are successfully able to modify the length of time the receptor remains in the blood stream.

PEGylation of an artificial O₂ and CO receptor: synthesis, characterisation and pharmacokinetic study
Takunori Ueda, Hiroaki Kitagishi and Koji Kano
Org. Biomol. Chem., 2012, 10, 4337-4347
DOI: 10.1039/C2OB07044H

The inside cover highlights the work of Nuno Maulide and co-workers, who present a new protocol for the direct 2-electron oxidative Umpolung of halide salts with commercially available sulfoxide. This means that electrophilic halogenations (including halolactonisations) can proceed directly from the corresponding sodium salts.

Sulfoxide-mediated Umpolung of alkali halide salts
Sebastian Klimczyk, Xueliang Huang, Christophe Farès and Nuno Maulide
Org. Biomol. Chem., 2012, 10, 4327-4329
DOI: 10.1039/C2OB25459J

Both of these articles are free to access for 6 weeks, so it’s easy to have a read.

You might also be interested in this perspective by Oskari K. Karjalainen and Ari M. P. Koskinen on the diastereoselective synthesis of vicinal amino alcohols.

View the complete issue here

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OBC issue 21: Novel dafachronic acids and macrocyclic aromatic pentamers on the covers

10 May 2012

OBC issue 21 has now landed, and you can find it here….

Hans-Joachim Knölker and co-workers present the stereoselective synthesis of several (25S)-dafachronic acids using an orthogonally diprotected diol as a relay compound. In addition Knölker et al. discuss the hormonal activity of the novel (25S)-dafachronic acids.

Stereoselective synthesis and hormonal activity of novel dafachronic acids and naturally occurring steroids isolated from corals
Ratni Saini, Sebastian Boland, Olga Kataeva, Arndt W. Schmidt, Teymuras V. Kurzchalia and Hans-Joachim Knölker
Org. Biomol. Chem., 2012, 10, 4159-4163
DOI: 10.1039/C2OB25394A

This impressive inside front cover highlights the work of Huaqiang Zeng et al. describing the ability of tetrabutylammonium salts to mediate an efficient mono-/di-demethylation in H-bonded macrocyclic aromatic pentamers, which occur in a chemo- and regionselective fashion.

Folding-promoted TBAX-mediated selective demethylation of methoxybenzene-based macrocyclic aromatic pentamers
Zhiyun Du, Bo Qin , Chang Sun, Ying Liu, Xi Zheng, Kun Zhang, Allan H. Conney and Huaqiang Zeng
Org. Biomol. Chem., 2012, 10, 4164-4171
DOI: 10.1039/C2OB25160D

Take a closer look at both of these articles; they’re free to access for the next 6 weeks!

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Palladium-catalysed aminosulfonylation and the design and synthesis of screening libraries on the cover of issue 20

04 May 2012

The covers of this week’s OBC issue are brought to you by Michael C. Willis et al. and Rohan A. Davis et al.

The front cover highlights the work of Michael C. Willis et al. who demonstrate that it is possible to construct C–SO₂–N linkages using palladium-catalysed aminosulfonylation processes.

Palladium-catalysed aminosulfonylation of aryl-, alkenyl- and heteroaryl halides: scope of the three-component synthesis of N-aminosulfonamides
Edward J. Emmett, Charlotte S. Richards-Taylor, Bao Nguyen, Alfonso Garcia-Rubia, Barry R. Hayter and Michael C. Willis
DOI: 10.1039/C2OB07034K

The inside front cover shows work from Rohan A. Davis et al. who present the design and synthesis of two screening libraries utilising the muurolane natural product scaffold from the plant E. mitchellii.

Design and synthesis of screening libraries based on the muurolane natural product scaffold
Emma C. Barnes, Vanida Choomuenwai, Katherine T. Andrews, Ronald J. Quinn and Rohan A. Davis
DOI: 10.1039/C2OB00029F

Don’t forget, access to these cover articles is FREE for the next 6 weeks.

Also in this issue is the HOT article ‘Synthetic UDP-galactofuranose analogs reveal critical enzyme–substrate interactions in GlfT2-catalyzed mycobacterial galactan assembly‘ which was highlighted in the C&EN news story ‘Determining Sugar Sequence Fidelity‘.

Find all of issue 20 here

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Issue 19 online with quantum mechanical tunnelling & 2-substituted 3-bromopyrrolidines on the covers

24 Apr 2012

On the front cover is this HOT Emerging Areaarticle from Peter R. Schreiner and co-workers (Justus-Liebig University, Germany) who discuss quantum mechanical tunnelling and provide an overview of the importance of tunnelling in organic chemical reactions.
Discussion includes:

a brief history of tunnelling
hydrogen tunnelling
carbon tunnelling
heteroatom tunnelling

Tunnelling control of chemical reactions – the organic chemist’s perspective
David Ley, Dennis Gerbig and Peter R. Schreiner
Org. Biomol. Chem., 2012, 10, 3781-3790
DOI: 10.1039/C2OB07170C

On the inside front cover is this Communication, from Ying-Yeung Yeung and colleagues at National University of Singapore, where a facile and highly enantioselective route to 2-substituted 3-bromopyrrolidines is presented. The authors demonstrate how these can be reached via the bromo-aminocyclisation of 1,2-disubstituted olefinic amides using amino-thiocarbamates as a catalyst. This is also part of our growing Organocatalysis web collection.

A highly enantioselective approach towards 2-substituted 3-bromopyrrolidines
Jie Chen, Ling Zhou and Ying-Yeung Yeung
Org. Biomol. Chem., 2012, 10, 3808-3811
DOI: 10.1039/C2OB25327E

Both of these cover articles will be free to access for the next 6 weeks.

Also in this issue:

A perspectiveby Alessandro Massi and Daniele Nanni:
Thiol–yne coupling: revisiting old concepts as a breakthrough for up-to-date applications

And 2 HOT articles that are still free to access for another 3 weeks

Diastereoselective alkylation reactions of 1-methylcyclohexa-2,5-diene-1-carboxylic acid
Mark C. Elliott et al.

Glycosylated diazeniumdiolate-based oleanolic acid derivatives: synthesis, in vitro and in vivo biological evaluation as anti-human hepatocellular carcinoma agents
Yihua Zhang et al.

View the entire issue HERE, it’s full of lots of great content!

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Chiral recognition of carbon nanoforms & 3-alkyl enol mimic inhibitors on the cover of OBC issue 18

12 Apr 2012

We are pleased to present to you OBC issue 18, 2012

Emilio M. Pérez and Nazario Martín present an Emerging area article providing an overview of some of the few successful examples of chiral recognition of carbon nanoforms, highlighting their common features with the aim of helping to develop general trends for the design of new generations of hosts.

Chiral recognition of carbon nanoforms
Emilio M. Pérez and Nazario Martín
Org. Biomol. Chem., 2012, 10, 3577–3583
DOI: 10.1039/C2OB07159B

The inside front cover illustrates work by Concepción González-Bello and co-workers at Universidad de Santiago de Compostela and University of Newcastle upon Tyne, who synthesised several 3-alkylaryl mimics of the enol intermediate in the the reversible dehydration reaction of 3-dehydroquinic acid, which is catalysed by type II dehydroquinase, to investigate the effect on the inhibition potency of replacing the oxygen atom in the side chain by a carbon atom.

Synthesis of 3-alkyl enol mimics inhibitors of type II dehydroquinase: factors influencing their inhibition potency
Beatriz Blanco, Antía Sedes, Antonio Peón, Heather Lamb, Alastair R. Hawkins, Luis Castedo and Concepción González-Bello
Org. Biomol. Chem., 2012, 10, 3662–3676
DOI: 10.1039/C2OB07081B

Both of these articles are free to access for 6 weeks so get your hands on them today!

Also in this issue:

A perspective by María Paz Muñoz covering the progress in transition metal-catalysed intermolecular reaction of allenes with oxygen nucleophiles, analysing the intermolecular metal-catalysed reaction of allenes using palladium, iridium, rhodium, ruthenium, gold and platinum, in the presence of alcohols, water or carboxylic acids, and the mechanistic implications of these processes depending on the metal used.

Transition metal-catalysed intermolecular reaction of allenes with oxygen nucleophiles: a perspective María Paz Muñoz
Org. Biomol. Chem., 2012,
DOI: 10.1039/C2OB07128B

The HOT article :
A convenient biomimetic synthesis of optically active putative neurotoxic metabolites of MDMA (“ecstasy”) from R-(−)- and S-(+)-N-methyl-α-methyldopamine precursors
Claire-Marie Martinez, Anne Neudörffer and Martine Largeron
DOI: 10.1039/C2OB25245G

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Promiscuous enantioselective lactamase activity on the cover of OBC issue 17

04 Apr 2012

This week’s OBC cover highlights the work of Aurelio Hidalgoand co-workers at the Center for Molecular Biology, whose paper describes the promiscuous enantioselective (−)-γ-lactamase activity in Pseudomonas fluorescensesterase I. In the paper Aurelio Hidalgoet al. show how the introduction of a mutation to the wild esterase improved the reaction turnover without affecting the enantioselectivity. Read the paper to find out more…..

This paper is FREE to access for the next 6 weeks, so why not take a look at it.

Promiscuous enantioselective (−)-γ-lactamase activity in the Pseudomonas fluorescensesterase I
Leticia L. Torres, Anna Schließmann, Marlen Schmidt, Noella Silva-Martin, Juan A. Hermoso, José Berenguer, Uwe T. Bornscheuer and Aurelio Hidalgo
Org. Biomol. Chem., 2012, 10, 3388-3392
DOI: 10.1039/C2OB06887G

Also in this issue:

A review:

Making expensive dirhodium(II) catalysts cheaper: Rh(II) recycling methods
Nuno R. Candeias, Carlos A. M. Afonso and Pedro M. P. Gois
Org. Biomol. Chem., 2012, 10, 3357-3378
DOI: 10.1039/C2OB06731E

A HOT article:

Copper-mediated domino synthesis of pyrimido[4,5-b]carbazolones via Ullmann N-arylation and aerobic oxidative C–H amidation
Devanga K. Sreenivas, Nagarajan Ramkumar and Rajagopal Nagarajan
Org. Biomol. Chem., 2012, 10, 3417-3423
DOI: 10.1039/C2OB07179G

View the entire issue HERE

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Take a stroll down memory lane with Organic & Biomolecular Chemistry on our 10th anniversary

29 Mar 2012

In our continued countdown to Organic & Biomolecular Chemistry‘s 10th anniversary issue we have had a look back at some of the art work that has appeared on our covers through the years. Below are the front covers of issue 1 and the work that featured on them for each year since the inception of OBC. What’s your favourite?

These stylish old school covers (right) were originally seen in 2003 & 2004 on volumes 1 & 2 respectively.

Volume 3:
Free: New chiral anion mediated asymmetric chemistry
Jérôme Lacour and Richard Frantz
Org. Biomol. Chem., 2005, 3, 15–19
DOI: 10.1039/B413554G

Volume 4:
Free: Artificial ribonucleases
Teija Niittymäki and Harri Lönnberg
Org. Biomol. Chem., 2006, 4, 15–25
DOI: 10.1039/B509022A

Volume 5:
Free: Synthesis of protein–polymer conjugates
Karina L. Heredia and Heather D. Maynard
Org. Biomol. Chem., 2007, 5, 45–53
DOI: 10.1039/B612355D

Volume 6:
Free: Metallo-nucleosides: synthesis and biological evaluation of hexacarbonyl dicobalt 5-alkynyl-2′-deoxyuridines
Craig D. Sergeant et al.

Org. Biomol. Chem., 2008, 6, 73–80
DOI: 10.1039/B713371E

Volume 7:
Free: Chemical approach toward efficient DNA methylation analysis
Akimitsu Okamoto
Org. Biomol. Chem., 2009, 7, 21–26
DOI: 10.1039/B813595A

Volume 8:
Free: Synthesis and biological evaluation of phosphatidylinositol phosphate affinity probes
Stuart J. Conway et al.

Org. Biomol. Chem., 2010, 8, 66–76
DOI: 10.1039/B913399B

Volume 9:
Free: Practical access to highly enantioenriched quaternary carbon Michael adducts using simple organocatalysts
Thomas C. Nugent, Mohammad Shoaib and Amna Shoaib
Org. Biomol. Chem., 2011, 9, 52–56
DOI: 10.1039/C0OB00822B

Volume 10:
Free: Synthesis of enantioenriched γ-quaternary cycloheptenones using a combined allylic alkylation/Stork–Danheiser approach: preparation of mono-, bi-, and tricyclic systems
Nathan B. Bennett et al.

Org. Biomol. Chem., 2012, 10, 56–59
DOI: 10.1039/C1OB06189E

All of these articles are FREE to access so if you missed them the first time round why not have a read now. In fact, why not have a look at the whole of the issue? All the content from each issue 1 is now FREE to access so dive in and enjoy:

Volume: 1 2 3 4 5 6 7 8 9 10

Do you have a favourite cover from our 10 years? Why not share it with us by leaving a comment below.

Interested in having your work featured on a cover? Submit your work to us and show us your artwork.

Missed our other 10th anniversary posts? Take a look here for some of our top cited work.

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OBC issue 16 has landed!

28 Mar 2012

The outside front cover of this week’s OBC is a communication from Barbara Zajcand colleagues at The City College and The City University of New York presenting a mild and efficient synthesis of 1-aryl-1-fluoroethenes from benzothiazolyl (aryl)fluoromethyl sulfones and paraformaldehyde, under DBU- or Cs₂CO₃-mediated conditions at room temperature.

Expedient synthesis of α-substituted fluoroethenes
Samir K. Mandal, Arun K. Ghosh, Rakesh Kumar and Barbara Zajc
Org. Biomol. Chem., 2012, 10, 3164–3167
DOI: 10.1039/C2OB07031F

The inside front cover is work from Keisuke Kato et al. at Toho University on the cyclization–carbonylation–cyclization coupling reaction of γ-propynyl-1,3-diketones catalysed by palladium(II)-bisoxazoline complexes to give symmetrical ketones bearing two oxabicyclic groups in moderate to excellent yields.

Cyclization–carbonylation–cyclization coupling reaction of γ-propynyl-1,3-diketones with palladium(II)-bisoxazoline catalyst
Taichi Kusakabe, Yasuko Kawai, Rong Shen, Tomoyuki Mochida and Keisuke Kato
Org. Biomol. Chem., 2012, 10, 3192–3194
DOI: 10.1039/C2OB07016B

Also in this issue:

Review:

Recent advances and applications of iridium-catalysed asymmetric allylic substitution by Paolo Tosatti and co-workers

Hot articles:

Electrophilicity of α-oxo gold carbene intermediates: halogen abstractions from halogenated solvents leading to the formation of chloro/bromomethyl ketones
Weimin He, Longyong Xie, Yingying Xu, Jiannan Xiang and Liming Zhang

Highly enantioselective [4 + 2] cycloadditions of allenoates and dual activated olefins catalyzed by N-acyl aminophosphines
Hua Xiao, Zhuo Chai, Dongdong Cao, Hongyu Wang, Jinghao Chen and Gang Zhao

Enantioselective synthesis of fluorene derivatives by chiral N-triflyl phosphoramide catalyzed double Friedel–Crafts alkylation reaction
Shou-Guo Wang, Long Han, Mi Zeng, Feng-Lai Sun, Wei Zhang and Shu-Li You

Hydrogen tunnelling influences the isomerisation of some small radicals of interstellar importance. A theoretical investigation
Tianfang Wang and John H. Bowie

See the rest HERE….

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An aerobic copper relay race and pharmacological chaperones for Gaucher disease treatment on the OBC covers

21 Mar 2012

This week’s issue of OBC features art work from Qing Xu and Xin-Shan Ye et al.

Qing Xu and colleagues from Wenzhou University have developed a green copper catalyzed N-alkylation method for various amides and amines with alcohols, employing aerobic oxidation of the alcohols to aldehydes for a more effective way of activating the alcohols. This advantageous method uses a ligand-free catalyst and its only byproduct is water!

Copper-catalyzed N-alkylation of amides and amines with alcohols employing the aerobic relay race methodology
Qiang Li, Songjian Fan, Qing Sun, Haiwen Tian, Xiaochun Yu and Qing Xu
Org. Biomol. Chem., DOI: 10.1039/C1OB06743E

Xin-Shan Ye and co-workers at Peking University and University of Oxford have designed a concise route to a series of N-substituted ε-hexonolactams employing a tandem ring-expansion as the key step. These novel N-alkylated iminosugars are promising pharmacological chaperones for the treatment of N370S mutant Gaucher disease.

Synthesis of N-substituted ε-hexonolactams as pharmacological chaperones for the treatment of N370S mutant Gaucher disease
Guan-Nan Wang, Gabriele Twigg, Terry D. Butters, Siwei Zhang, Liangren Zhang, Li-He Zhang and Xin-Shan Ye
Org. Biomol. Chem., DOI: 10.1039/C2OB06987C

Both of these articles can be accessed for free for the next 6 weeks!

Other interesting articles in this issue are:

A perspective by Alfredo Ricci et al. about bioinspired organocatalytic asymmetric reactions

and 2 HOT articles which are free to access for the next 4 weeks:

Fluorimetric detection of Mg²⁺and DNA with 9-(alkoxyphenyl)benzo[b]quinolizinium derivatives
Maoqun Tian, Heiko Ihmels and Shite Ye
Org. Biomol. Chem., DOI: 10.1039/C2OB06948B

Substituted oxines inhibit endothelial cell proliferation and angiogenesis
Shridhar Bhat, Joong Sup Shim, Feiran Zhang, Curtis Robert Chong and Jun O. Liu
Org. Biomol. Chem., DOI: 10.1039/C2OB06978D

If you liked those why not view the rest of the issue HERE!

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Modern microwave chemistry opportunities to develop new antibiotics and antiviral drugs on OBC Issue 14’s cover

15 Mar 2012

Welcome to OBC issue 14, 2012

On the cover features work by Mats Larhed et al. at Uppsala University, Sweden, who describe in this highly topical review the use of controlled microwave heating in discovery chemistry to combat four of the most prevalent and serious infectious diseases: tuberculosis, HIV/AIDS, malaria and hepatitis C.

This Perspective highlights the large number of diverse chemical transformations that can be accomplished using controlled and automated single-mode microwave heating.

Why not read it now, it will be FREE to access for the next 6 weeks!

Microwave-assisted synthesis of small molecules targeting the infectious diseases tuberculosis, HIV/AIDS, malaria and hepatitis C
Johan Gising, Luke R. Odell and Mats Larhed
Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06833H, Perspective

Also in this issue, a Hot Article by Robert M. Strongin et al. on a cysteine selective indicator based on a seminaphthofluorescein, and much more!

View the full issue here

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