Archive for January, 2012

Have you seen our recent review articles? New routes to indoles, carbohydrates for drug discovery, artificial nucleobases & more

During 2011 we published a number of topical reviews on a wide range of topics by expert researchers in their fields.  We’ve collected some of them below but take a look here for the whole list, we hope you’ll find something interesting in your area!

Sequential one-pot combination of multi-component and multi-catalysis cascade reactions: an emerging technology in organic synthesis
Dhevalapally B. Ramachary and Sangeeta Jain
DOI: 10.1039/C0OB00611D

Carbohydrate chemistry in drug discovery
M. Carmen Galan, David Benito-Alifonso and Gregory M. Watt
DOI: 10.1039/C0OB01017K

Recent advances in indole syntheses: New routes for a classic target
Rubén Vicente
DOI: 10.1039/C1OB05750B

Chiral separation by enantioselective liquid–liquid extraction
Boelo Schuur, Bastiaan J. V. Verkuijl, Adriaan J. Minnaard, Johannes G. de Vries, Hero J. Heeres and Ben L. Feringa
DOI: 10.1039/C0OB00610F

Cascade polycyclisations in natural product synthesis
Edward A. Anderson
DOI: 10.1039/C1OB05212H

Targeting DNA base pair mismatch with artificial nucleobases. Advances and perspectives in triple helix strategy
Vincent Malnuit, Maria Duca and Rachid Benhida
DOI: 10.1039/C0OB00418A

Unlocked nucleic acid – an RNA modification with broad potential
Anna Pasternak and Jesper Wengel
DOI: 10.1039/C0OB01085E

Nitrogen cation–π interactions in asymmetric organocatalytic synthesis
Shinji Yamada and John S. Fossey
DOI: 10.1039/C1OB05228D

If you have an idea for a review article that hasn’t been covered and you would like to see included, contact the Editorial Office – we’d love to hear from you.

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Synthesising ureas from CO2, recognition of oxoanions and cross-metathesis for heterocycles in Issue 7

The cool images on this week’s cover are from Giuseppe Resnati, NFMLab, and James C. Anderson, UCL.

Resnati and colleagues have conducted an NMR study of phosphate oxoanion binding of a 2-iodo-imidazolium receptor with charge assisted halogen bonding, finding a surprisingly strong binding constant for phosphate anions, their work is highlighted on the outside front cover.

2-Iodo-imidazolium receptor binds oxoanions via charge-assisted halogen bonding
Massimo Cametti, Kari Raatikainen, Pierangelo Metrangolo, Tullio Pilati, Giancarlo Terraneo and Giuseppe Resnati
DOI: 10.1039/C1OB06524F

On a completely different topic, Anderson and Moreno have been using CO2 to produce ureas at ambient conditions, using 12- and 14- electron titanium imido complexes:

Synthesis of ureas from titanium imido complexes using CO2 as a C-1 reagent at ambient temperature and pressure
James C. Anderson and Rafael Bou Moreno
DOI: 10.1039/C1OB06576A

As well as these the issue also contains a review from Tim Donohoe on olefin cross-metathesis for heterocycle synthesis and plenty of other hot articles, take a look…

Hot articles in this issue:

Some cyclization reactions of 1,3-diphenylbenzo[e][1,2,4]triazin-7(1H)-one: preparation and computational analysis of non symmetrical zwitterionic biscyanines
Theodosia A. Ioannou, Panayiotis A. Koutentis, Harry Krassos, Georgia Loizou and Daniele Lo Re
DOI: 10.1039/C1OB06622F

Oxidative Prins and Prins/Friedel–Crafts cyclizations for the stereoselective synthesis of dioxabicycles and hexahydro-1H-benzo[f]isochromenes via the benzylic C–H activation
B. V. Subba Reddy, Prashant Borkar, J. S. Yadav, P. Purushotham Reddy, A. C. Kunwar, B. Sridhar and René Grée
DOI: 10.1039/C1OB06489D

Chemoenzymatic synthesis of a mixed phosphine–phosphine oxide catalyst and its application to asymmetric allylation of aldehydes and hydrogenation of alkenes
Derek R. Boyd, Mark Bell, Katherine S. Dunne, Brian Kelly, Paul J. Stevenson, John F. Malone and Christopher C. R. Allen
DOI: 10.1039/C1OB06599H

James C. Anderson and Rafael Bou Moreno
Org. Biomol. Chem., 2012, 10, 1334-1338
DOI: 10.1039/C1OB06576A

Certain 12- and 14- electron titanium imido complexes

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Top 10 Communication articles from Organic & Biomolecular Chemistry

Below are the top 10 cited OBC Communications ever – take a look and let us know what your favourites are:

A donor–acceptor substituted molecular motor: unidirectional rotation driven by visible light
Richard A. van Delden, Nagatoshi Koumura, Annemarie Schoevaars, Auke Meetsma and Ben L. Feringa
DOI: 10.1039/B209378B

The small peptide-catalyzed direct asymmetric aldol reaction in water
Pawel Dziedzic, Weibiao Zou, Jonas Háfren and Armando Córdova
DOI: 10.1039/B515880J

Improving conversion and enantioselectivity in hydrogenation by combining different monodentate phosphoramidites; a new combinatorial approach in asymmetric catalysis
Diego Peña, Adriaan J. Minnaard, Jeroen A. F. Boogers, André H. M. de Vries, Johannes G. de Vries and Ben L. Feringa
DOI: 10.1039/B302097E

Accelerated asymmetric transfer hydrogenation of aromatic ketones in water
Xiaofeng Wu, Xiaoguang Li, William Hems, Frank King and Jianliang Xiao
DOI: 10.1039/B403627A

Direct asymmetric three-component organocatalytic anti-selective Mannich reactions in a purely aqueous system
Lili Cheng, Xiaoyu Wu and Yixin Lu
DOI: 10.1039/B701579H

A highly selective and sensitive fluorescent PET (photoinduced electron transfer) chemosensor for Zn(II)
Thorfinnur Gunnlaugsson, T. Clive Lee and Raman Parkesh
DOI: 10.1039/B309569J

Enantioselective construction of quaternary carbon centre catalysed by bifunctional organocatalyst
Tian-Yu Liu, Jun Long, Bang-Jing Li, Lin Jiang, Rui Li, Yong Wu, Li-Sheng Ding and Ying-Chun Chen
DOI: 10.1039/B605871J

A chiral molecular recognition approach to the formation of optically active quaternary centres in aza-Henry reactions
Kristian Rahbek Knudsen and Karl Anker Jørgensen
DOI: 10.1039/B500618J

Direct palladium-catalyzed alkenylation, benzylation and alkylation of ethyl oxazole-4-carboxylate with alkenyl-, benzyl- and alkyl halides
Cécile Verrier, Christophe Hoarau and Francis Marsais
DOI: 10.1039/B816374J

Organocatalytic asymmetric epoxidation reactions in water–alcohol solutions
Wei Zhuang, Mauro Marigo and Karl Anker Jørgensen
DOI: 10.1039/B512542A

If you have highly important work that would benefit from urgent publication in synthetic, biomolecular or physical organic chemistry why not consider submitting a Communication article to OBC? Find out more…

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Top ten most accessed articles in November

This month sees the following articles in Organic & Biomolecular Chemistry that are in the top ten most accessed:

Preparation and reactivity of imino glycals: stereocontrolled, divergent approach to imino sugars
Paul J. Dransfield, Paul M. Gore, Ivan Prokeš, Michael Shipman and Alexandra M. Z. Slawin
Org. Biomol. Chem., 2003, 1, 2723-2733
DOI: 10.1039/B303817C

A one-pot catalysis: the strategic classification with some recent examples
Nitin T. Patil, Valmik S. Shinde and Balakrishna Gajula
Org. Biomol. Chem., 2012, 10, 211-224
DOI: 10.1039/C1OB06432K

An organocatalytic approach to enantiomerically enriched α-arylcyclohexenones and cyclohexanones
Sara Duce, María Jorge, Inés Alonso, José Luis García Ruano and M. Belén Cid
Org. Biomol. Chem., 2011, 9, 8253-8260
DOI: 10.1039/C1OB06356A

Synthesis of oxindoles via visible light photoredox catalysis
Xuhui Ju, Yan Liang, Pingjing Jia, Weifei Li and Wei Yu
Org. Biomol. Chem., 2012, 10, 498-501
DOI: 10.1039/C1OB06652H

Squaramide-catalyzed enantioselective Michael addition of malononitrile to chalcones
Wen Yang, Yang Jia and Da-Ming Du
Org. Biomol. Chem., 2012, 10, 332-338
DOI: 10.1039/C1OB06302B

Organocatalytic asymmetric tandem condensation–intramolecular rearrangement–protonation: an approach to optically active α-amino thioester derivatives
Francesca Capitta, Angelo Frongia, Pier Paolo Piras, Patrizia Pitzanti and Francesco Secci
Org. Biomol. Chem., 2012, 10, 490-494
DOI: 10.1039/C1OB06623D

Oxidative Prins and Prins/Friedel–Crafts cyclizations for the stereoselective synthesis of dioxabicycles and hexahydro-1H-benzo[f]isochromenes via the benzylic C–H activation
B. V. Subba Reddy, Prashant Borkar, J. S. Yadav, P. Purushotham Reddy, A. C. Kunwar, B. Sridhar and René Grée
Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C1OB06489D

Gold-mediated bifunctional modification of oligosaccharides via a three-component coupling reaction
Karen Ka-Yan Kung, Gai-Li Li, Lan Zou, Hiu-Chi Chong, Yun-Chung Leung, Ka-Hing Wong, Vanessa Kar-Yan Lo, Chi-Ming Che and Man-Kin Wong
Org. Biomol. Chem., 2012, 10, 925-930
DOI: 10.1039/C1OB06429K

Asymmetric organocatalysis
Jayasree Seayad and Benjamin List
Org. Biomol. Chem., 2005, 3, 719-724
DOI: 10.1039/B415217B

Indolizinones as synthetic scaffolds: fundamental reactivity and the relay of stereochemical information
Alison R. Hardin Narayan and Richmond Sarpong
Org. Biomol. Chem., 2012, 10, 70-78
DOI: 10.1039/C1OB06423A

Why not take a look at the articles today and blog your thoughts and comments below.

Fancy submitting an article to Organic & Biomolecular Chemistry? Then why not submit to us today or alternatively email us your suggestions.

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Imaging Norepinephrine transporters (NET) with self-reporting dyes

One area of research developed in Dr James N. Wilson‘s lab at the University of Miami (Florida, USA) is aimed at elucidating the complex molecular mechanisms of intercellular communication, via the development of fluorescent analogues of neuroactive compounds.

In their latest OBC communication,  Wilson et al. describe the synthesis, characterization and interaction of cell lines with novel dimeric stilbazolium-based dyes that probe the functional limit of norepinephrine transport (NET) in cells. Upon exposure to different NET proteins, these environmentally sensitive dyes turn on the fluorescence and their binding to NET can be monitored using fluorescence microscopy

This article will be FREE to access for the next 4 weeks.
Why not read it now and let us know what you think by posting a comment below!

Probing the functional limits of the norepinephrine transporter with self-reporting, fluorescent stilbazolium dimers
Erika L. Smith, Adrienne S. Brown, Edward Adjaye-Mensah and James N. Wilson
Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06796J, Communication

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Cyclocondensation reactions of the heterocyclic scaffold benzotriazinone lead to several highly coloured acenes

In this OBC Hot Article, Panayiotis Koutentis and co-workers at the University of Cyprus show how 1,3-Diphenylbenzo[e][1,2,4]triazin-7(1H)-one reacts with various bisnucleophiles to give a variety of deeply coloured polyazaacenes, including two zwitterionic analogues.

 

Read the article to find out more about the preparation, mechanistic considerations and photophysical studies of these new heterocyclic ring systems derived from benzo[1,2,4]triazin-7-ones.

FREE to access for a period of 4 weeks!




Some cyclization reactions of 1,3-diphenylbenzo[e][1,2,4]triazin-7(1H)-one: preparation and computational analysis of non symmetrical zwitterionic biscyanines
Theodosia A. Ioannou, Panayiotis A. Koutentis, Harry Krassos, Georgia Loizou and Daniele Lo Re
Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C1OB06622F, Paper

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Issue 6 online – including water-binding aquafoldamers, fluorinated probes and glycosylated 5-hydroxylysine

On the outside front cover of this week’s issue is a hot article from Huaiqing Zhao, National University of Singapore, et al. on a series of water-binding aquafoldamers with potential use in recognizing topologically diverse larger water clusters and as synthetic water channels. This article is part of our forthcoming themed issue on Foldamer Chemistry.

Synthesis, structural investigation and computational modelling of water-binding aquafoldamers
Huaiqing Zhao, Wei Qiang Ong, Xiao Fang, Feng Zhou, Meng Ni Hii, Sam Fong Yau Li, Haibin Su and Huaqiang Zeng
DOI: 10.1039/C1OB06609A

The inside front cover is work from Jonathan Guimond-Tremblay, Université Laval, et al. on the synthesis of three monofluorinated dimyristoylphosphatidylcholine derivatives for use as probes in 19F NMR studies to study the effects of drugs and peptides on model membranes.

Synthesis and properties of monofluorinated dimyristoylphosphatidylcholine derivatives: Potential fluorinated probes for the study of membrane topology
Jonathan Guimond-Tremblay, Marie-Claude Gagnon, Jozy-Ann Pineault-Maltais, Vanessa Turcotte, Michèle Auger and Jean-François Paquin
DOI: 10.1039/C2OB06570C

The issue also includes a review on the synthesis of glycosylated (2S,5R)-hydroxylysine from Margaret Brimble and coworkers and a hot article from Valentina Cerulli et al., on a highly diastereoselective Ugi multicomponent reaction

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OBC celebrates its 10th year of publication

Image ©Shutterstock

We can’t quite believe it but this year Organic & Biomolecular Chemistry is going to be 10 years old!

To celebrate this we will be publishing an issue later this year that features some of the best work by chemists from across the broad scope of the journal, many of whom have served on our Editorial or Advisory Boards over the years.

Leading up to the issue we’ll be bringing you some of our ‘Top 10s’ from the journal…watch this space!

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Hot Emerging Area article: olefin cross-metathesis for the synthesis of heteroaromatic compounds

Timothy Donohoe et al. from the University of Oxford review recent developments in the synthesis of furan, pyrrole and pyridine heterocycles via cross-metathesis methods in this Emerging Area article.

It’s free to access for 4 weeks, so take a look…

Olefin cross-metathesis for the synthesis of heteroaromatic compounds
Timothy J. Donohoe, John F. Bower and Louis K. M. Chan
DOI: 10.1039/C2OB06659A

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HOT: chemoenzymatic synthesis of a mixed phosphine–phosphine oxide organocatalyst and its applications

This OBC Hot Article by Paul J. Stevenson and co-workers at Queens University (Belfast) and Celtic Catalysts Ltd (Dublin) highlights the chemoenzymatic synthesis of a Lewis basic phosphine–phosphine oxide organocatalyst from a cis-dihydrodiol metabolite of bromobenzene.

Of particular interest is the impressively facile Arbuzov [2,3]-sigmatropic rearrangement reaction that the team observed – a pivotal step for this synthesis.

  • Find out about the applications of this new catalyst…
  • Read the article for Free for the next 4 weeks…

Reference
Chemoenzymatic synthesis of a mixed phosphine–phosphine oxide catalyst and its application to asymmetric allylation of aldehydes and hydrogenation of alkenes
Derek R. Boyd, Mark Bell, Katherine S. Dunne, Brian Kelly, Paul J. Stevenson, John F. Malone and Christopher C. R. Allen
Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C1OB06599H, Paper

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