Archive for the ‘Reviews’ Category

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

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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Asymmetric catalytic Mannich-type reaction of hydrazones using Zn(II) complexes on the cover of OBC issue 13

The cover of this week’s OBC features work from Min Shi et al. at Shanghai Institute of Organic Chemistry and Texas Tech University, who have used chiral zinc(II)–imidazoline–phosphine complexes in a novel catalytic system for the asymmetric Mannich-type difluorination of hydrazones with difluoroenoxysilanes.

Asymmetric catalytic Mannich-type reaction of hydrazones with difluoroenoxysilanes using imidazoline-anchored phosphine ligand–zinc(II) complexes
Zhiliang Yuan, Liangyong Mei, Yin Wei, Min Shi, Padmanabha V. Kattamuri, Patrick McDowell and Guigen Li
Org. Biomol. Chem., 2012, 10, 2509-2513
DOI: 10.1039/C2OB07022G

Read the full Communication; it is FREE to access for the next 6 weeks.

This issue also contains:

A Perspective review article: On a so-called “kinetic anomeric effect” in chemical glycosylation, by Ian Cumpstey

as well as the HOT article:

Synthesis and protein binding studies of a peptide fragment of clathrin assembly protein AP180 bearing an O-linked β-N-acetylglucosaminyl-6-phosphate modification
Mark E. Graham, Robin S. Stone, Phillip J. Robinson and Richard J. Payne

If you liked these why not have a look at the rest of the issue here

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Hot Perspective: Using trichlorosilane for the organocatalysed reduction of ketimines

Following the recent highlight of topical reviews in OBC, here is our latest ‘Hot Perspective’:

  •  read about the most advanced developments on Trichlorosilane mediated asymmetric reductions of the C=N bond in this review article by Simon Jones and Christopher J. A. Warner.

Concise but thorough, the review will take you through efficient and economical ways to access chiral amines via the trichlorosilane mediated organocatalytic reduction of ketimines, and provide a direct quantitative comparison to transition-metal mediated process.

Trichlorosilane mediated asymmetric reductions of the C=N bond
Simon Jones and Christopher J. A. Warner
Org. Biomol. Chem., 2012, 10, 2189-2200
DOI: 10.1039/C2OB06854K, Perspective

This Perspective will be FREE to access for the next 4 weeks 
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Top 10 Perspective articles from Organic & Biomolecular Chemistry

Continuing with our countdown to OBC’s 10th anniversary celebratory issue we’ve made the top cited* Perpsective articles from the journal free to access for one week:

1. Recognition and activation by ureas and thioureas: stereoselective reactions using ureas and thioureas as hydrogen-bonding donors
Yoshiji Takemoto
DOI: 10.1039/B511216H

2. Bifunctional transition metal-based molecular catalysts for asymmetric syntheses
Takao Ikariya,  Kunihiko Murata and Ryoji Noyori
DOI: 10.1039/B513564H

3. Analysis of the reactions used for the preparation of drug candidate molecules
John S. Carey,  David Laffan, Colin Thomson and Mike T. Williams
DOI: 10.1039/B602413K

4. Density functional theory with dispersion corrections for supramolecular structures, aggregates, and complexes of (bio)organic molecules
Stefan Grimme,  Jens Antony, Tobias Schwabe and Christian Mück-Lichtenfeld
DOI: 10.1039/B615319B

5. Mechanistic aspects of transition metal catalysed 1,6-diene and 1,6-enyne cycloisomerisation reactions
Guy C. Lloyd-Jones
DOI: 10.1039/B209175P

6. Multivalency in supramolecular chemistry and nanofabrication
Alart Mulder,  Jurriaan Huskens and David N. Reinhoudt
DOI: 10.1039/B413971B

7. Porphyrin–fullerene linked systems as artificial photosynthetic mimics
Hiroshi Imahori
2004, DOI: 10.1039/B403024A

8. Ru complexes bearing bidentate carbenes: from innocent curiosity to uniquely effective catalysts for olefin metathesis
Amir H. Hoveyda,  Dennis G. Gillingham,  Joshua J. Van Veldhuizen,  Osamu Kataoka,  Steven B. Garber,  Jason S. Kingsbury and Joseph P. A. Harrity
DOI: 10.1039/B311496C

9. Molecular similarity: a key technique in molecular informatics
Andreas Bender and Robert C. Glen
DOI: 10.1039/B409813G

10. DNA-programmed assembly of nanostructures
Kurt V. Gothelf and Thomas H. LaBean
DOI: 10.1039/B510551J

  • Interested in joining in with a Perspective article for OBC? Why not get in contact – we’d love to hear your ideas.

*Top cited Perspective articles according to ISI on the 1st of February 2012

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Review on microwave synthesis of small molecules to target TB, HIV/AIDS, malaria and hepatitis C

Mats Larhed and colleagues from the University of Uppsala provide an extremely accessible introduction to microwave synthesis in this review article, demonstrating the use of single-mode microwave synthesis for laboratory-scale preparation of small molecules.  They focus of the synthesis of potential treatments of four of the world’s most infectious diseases; tuberculosis, HIV/AIDS, malaria and hepatitis C.


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
DOI: 10.1039/C2OB06833H

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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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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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Squaraine dyes for photodynamic therapy: reviewing the latest developments

Following our latest OBC Hot Article by Prof. Bradley D. Smith (available here), Squaraines are in the spotlight again in this review article by Danaboyina Ramaiah et al..

The Perspective highlights the recent developments of squaraines as PDT sensitizers, including:


  • Design principles
  • Squaraines as singlet oxygen generators
  • Squaraines as two-photon absorbing agents
  • Carrier systems for squaraine dyes
  • In vitro and in vivo studies of squaraine-PDT action

 
Timely and HOT, why not read this Perspective now – it will be FREE to access for the next 4 weeks




Squaraine dyes in PDT: from basic design to in vivo demonstration
Rekha R. Avirah, Dhanya T. Jayaram, Nagappanpillai Adarsh and Danaboyina Ramaiah
Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C1OB06588B, Perspective

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Hot emerging area: Transition metal-catalysed (4 + 3) cycloaddition reactions involving allyl cations

Israel Fernández and José Luis Mascareñas review novel intramolecular (4 +3)-cycloaddition reactions of allenedienes in this Emerging Area article, focussing on recent examples where the allene acts as an allylic-cation surrogate.  These methodologies overcome problems with previous strategies involving unstable allyl cation precursors or the need for stoichiometric activators and conformationally restricted dienes.

Areas covered include:

  • (4 + 3)-Cycloaddition reactions mediated by platinum(II) and gold(I) complexes
  • Aromaticity in the (4 + 3)-cycloaddition
  • Concerted vs. stepwise reaction mechanisms

As with all our hot research, this article will be free to access for 4 weeks – so take a look today:

Transition metal-catalysed (4 + 3) cycloaddition reactions involving allyl cations
Israel Fernández and José Luis Mascareñas
DOI: 10.1039/C1OB06604H

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Perspective: Organofluoro nucleophiles for enantioselective organocatalytic fluorination


‘While methods of electrophilic fluorination have been extensively developed to stereoselectively install fluorine atoms onto molecules, nucleophilic fluorination is a much less explored approach’, explains Associate Professor Choon-Hong Tan, from National University of Singapore.

In this concise review article, Choon-Hong and coll. highlight an emerging methodology of enatioselective C-C coupling via fluorocarbanion additions, which significantly expands the scope of enantio-enriched fluorine-containing compounds that can be synthesised. The recent advances in the application of organofluoro nucleophiles in organocatalysis are described.

Enantioselective organocatalytic fluorination using organofluoro nucleophiles
Yujun Zhao, Yuanhang Pan, Sui-Boon Derek Sim and Choon-Hong Tan
Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C1OB05840A, Perspective

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