Archive for the ‘Reviews’ Category

Emerging area: classifying one-pot catalysis

Take a look at this Emerging Area article from Nitin Patil et al. who propose a classification system to update the definition of one-pot catalysis.   They give readers recent examples of metal-metal, metal-organo and organo-organo catalytic systems that fall into the three categories of cooperative, relay and sequential one-pot catalysis.

The article will be free to access for the next four weeks:

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

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HOT: Systematic (chemical) space exploration – a challenge for synthetic chemists

Scaffold diversity of the organic chemistry universe

‘Chemists’ historical exploration of chemical space has been highly uneven and unsystematic’ write Adam Nelson and coworkers.  In this Perspective article they seek to pull together  synthetic strategies that have been designed to allow a more systematic discovery of biologically active small molecules, with particular emphasis on combinatorial strategies.

Areas covered:

  • The “build–couple–pair” approach
  • Ambiphile pairing reactions
  • Folding and branching pathways
  • Oligomer-based approaches to scaffold diversity

This hot article is free to access for the next four weeks – download today to read more on the ‘challenge for synthetic chemists in the twenty-first century’:

Towards the systematic exploration of chemical space
Mark Dow, Martin Fisher, Thomas James, Francesco Marchetti and Adam Nelson
DOI: 10.1039/C1OB06098H

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Perspective: Development and utilization of non-coding RNA–small molecule interactions

Wesleigh Georgianna and Douglas Young review the possibilities for small molecule regulation of non-coding RNA covering:

  • miRNA
  • siRNA
  • RNA aptamers
  • riboswitches
  • ribozymes

Download the article to find out more about regulating this novel target:

Development and utilization of non-coding RNA–small molecule interactions
Wesleigh E. Georgianna and Douglas D. Young
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C1OB06324C

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HOT Perspective: Effective synthetic routes to the lantibiotics peptides

In this ‘Hot’ OBC Perspective, Alethea Tabor (University College London, UK) provides an excellent overview of the recent advances in the chemical synthesis of lantibiotics, a field which has considerably moved on since the last review in the area in 2005 by W. A. van der Donk.

The approaches covered include:

  • solution-phase  and solid-phase synthesis
  •  biomimetic approaches
  •  biotransformation strategies

Keep up-to date with the synthesis of these structurally complex peptides possessing unique antibacterial properties and read this review article, FREE to access for the next 4 weeks*


The challenge of the lantibiotics: synthetic approaches to thioether-bridged peptides
Alethea B. Tabor
Org. Biomol. Chem., 2011, 9, 7606-7628
DOI: 10.1039/C1OB05946G

* upon a simple registration process for individual access

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On the cover: perspective on cation-pi interactions in asymmetric synthesis and alloxazine–cyclodextrin conjugates for sulfoxidations

On the outside cover of Issue 21 we have a hot perspective article from Shinji Yamada and John S. Fossey describing nitrogen cation-π interactions in asymmetric synthesis and summarises the areas where these interactions play an important role.

Areas covered:

  • Iminium–π interactions
  • Pyridinium–π interactions
  • Imidazolium, thiazolium and related structure–π interactions

Nitrogen cation–π interactions in asymmetric organocatalytic synthesis
Shinji Yamada and John S. Fossey
Org. Biomol. Chem., 2011, 9, 7275-7281
DOI: 10.1039/C1OB05228D

The inside cover highlights work from Radek Cibulka and Tomas Kraus et al. who have used four alloxazine–cyclodextrin conjugates as catalysts for enantioselective oxidation of prochiral sulfides to sulfoxides.  Their method avoids the problems of overoxidation to sulfones that sometimes occur when transition metal catalysts are used, and provides better enantioselectivity (up to 77% ee) than other sulfoxidation organocatalysts.

Alloxazine–cyclodextrin conjugates for organocatalytic enantioselective sulfoxidations
Viktor Mojr, Miloš Buděšínský, Radek Cibulka and Tomáš Kraus
Org. Biomol. Chem., 2011, 9, 7318-7326
DOI: 10.1039/C1OB05934C

Both articles are free to access for the next 6 weeks.

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Perspective: heterocycle synthesis via tandem copper cross-coupling reactions

Yunyun Liu and Jie-Ping Wan from Jiangxi Normal University in China review recent research progress in heterocycle syntheses using tandem reactions initiated by copper-catalysed coupling transformations.

Areas they include are:

  • Reactions initiated by C–N coupling
  • Reactions initiated by C–O coupling
  • Reactions initiated by C–S coupling
  • Reactions involving a double C–X coupling process

Our sister journal Chemical Society Reviews has just published a themed issue on cross-coupling reactions – why not take a look?

Tandem reactions initiated by copper-catalyzed cross-coupling: A new strategy towards heterocycle synthesis
Yunyun Liu and Jie-Ping Wan
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C1OB05769C

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Emerging Area: the versatility of the Photo-Deyhdro-Diels-Alder reaction

In this concise review article, Pablo Wessig and colleagues at University Potsdam (Germany) highlight the benefits of the Photo-Deyhdro-Diels-Alder (PDDA) reaction as a synthetically interesting and useful photochemical reaction. While often overlooked in the past, the PDDA reaction enables the synthesis of molecules which are often not accessible via the Diels–Alder (DA) or dehydro-Diels–Alder (DDA) reactions, thanks to the large amount of energy generated by the photoactivation of the reactants.

How would you use the PDDA reaction?

From phenylnaphthalenes, N-heterocyclic biaryls and naphthalenophanes, check out its considerable scope in this OBC article!

The photo-dehydro-Diels–Alder (PDDA) reaction
Pablo Wessig, Annika Matthes and Charlotte Pick
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C1OB06066J, Emerging Area

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Recent advances in indole syntheses: New routes for a classic target

This Perspective article from Rubén Vicente at the University of Oviedo, Spain, reviews the most relevant and inventive approaches towards the preparation of the ubiquitous indole motif in the last five years.

Areas covered in this review:

  • Indole syntheses from o-alkynylanilines and derivatives
  • Indole syntheses from o-haloanilines
  • Indole syntheses from o-alkynylhaloarenes or o-dihaloarenes
  • Indole syntheses from b-(pseudo)halostyrene derivatives
  • Indole syntheses from o-propargylanilines
  • Indole syntheses from acetophenone derivatives
  • Indole syntheses from arylhydrazines and related compounds
  • Indole syntheses via nitrene or carbene insertions
  • Indole syntheses via processes involving a C–C- or N–N-cleavage
  • Indole syntheses through C–H-bond functionalizations

Despite the impressive list of clever synthetic routes presented, Dr Vicente highlights that more sustainable and efficient routes are still needed for future developments – so why not take a look and get synthesising? The article is free to access for four weeks:

Recent advances in indole syntheses: New routes for a classic target
Rubén Vicente
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C1OB05750B, Perspective

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HOT: Bionanoparticles as building blocks

Nature has designed many biogenic systems with exquisite symmetries and complexities on the nanometer scale, such as viruses, ferritins and enzyme complexes. These structures have acted as building blocks on which researchers have been able to develop bionanoparticles with a wide variety of applications including biosensors, electronic nanodevices,  drug delivery agents and vaccine carriers, amongst others. 

In this OBC Perspective Qian Wang and colleagues highlight some of the recent progress in the chemical modification and molecular engineering of these bionanoparticles with the aim of sparking new discussions and inspiring the development of many new materials in the future.

Graphical abstract: Altering the landscape of viruses and bionanoparticles

Interested? Then why not read this comprehensive review now. It is free to download for the next four weeks!

Altering the landscape of viruses and bionanoparticles
L. Andrew Lee, Huong Giang Nguyen and Qian Wang
Org. Biomol. Chem., 2011, DOI: 10.1039/C1OB05700F

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Review: Dehydrotryptophan – a building block for peptide synthesis

Produced by microorganisms, marine organisms and plants, dehydrotriptophan and its derivatives are amino acids commonly found in peptide-based natural products, thereby prompting their use as a building block for peptide synthesis.

Although literature is available on the synthesis of dehydroamino acids, the focus on dehydrotriptophan has now been addressed by Margaret Brimble and coworkers (the University of Auckland, New Zealand) in this OBC Perspective, which highlights the different methods to synthesise the dehydrotryptophan-containing segment of naturally occurring peptides, amino acids and their derivatives.

Interested? Then why not read this comprehensive review now:
The synthesis of dehydrotryptophan and dehydrotryptophan-containing peptides Harveen Kaur, Amanda M. Heapy and Margaret A. Brimble
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C1OB05777D, Perspective

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