Author Archive

Countdown to OBC’s 10th anniversary continues with tin and aluminium!

Continuing our countdown to OBC’s 10th anniversary issue, we’ve collected together 10 tin and aluminium related articles published in the journal. Why? An old tradition in the UK is to give gifts of made of symbolic materials on significant wedding anniversaries, and the metals associated with a 10th wedding anniversary are tin and aluminium. Now, we don’t have any trinkets for you, but why not take a look at some of these interesting tin and aluminium-themed articles!

Effective 1,5-, 1,6- and 1,7-remote stereocontrol in reactions of alkoxy- and hydroxy-substituted allylstannanes with aldehydes
John S. Carey, Somhairle MacCormick, Steven J. Stanway, Aphiwat Teerawutgulrag and Eric J. Thomas
DOI: 10.1039/C0OB01084G

A selective, cell-permeable fluorescent probe for Al3+ in living cells
Lina Wang, Wenwu Qin, Xiaoliang Tang, Wei Dou, Weisheng Liu, Qingfeng Teng and Xiaojun Yao
DOI: 10.1039/C0OB00123F, Paper

Microwave-assisted regioselective ring opening of non-activated aziridines by lithium aluminium hydride
Sonja Stanković, Matthias D’hooghe and Norbert De Kimpe
DOI: 10.1039/C004960C

Synthesis of Biginelli dihydropyrimidinone derivatives with various substituents on aluminium-planted mesoporous silica catalyst
Hiroaki Murata, Haruro Ishitani and Masakazu Iwamoto
DOI: 10.1039/B920821F, Paper

Intramolecular carbolithiation reactions for the preparation of 3-alkenylpyrrolidines
Iain Coldham, Kathy N. Price and Richard E. Rathmell
DOI: 10.1039/B303670G

Rapid methylation on carbon frameworks useful for the synthesis of 11CH3-incorporated PET tracers: Pd(0)-mediated rapid coupling of methyl iodide with an alkenyltributylstannane leading to a 1-methylalkene
Takamitsu Hosoya, Kengo Sumi, Hisashi Doi, Masahiro Wakao and Masaaki Suzuki
DOI: 10.1039/B515215A

Aluminium triflate: a remarkable Lewis acid catalyst for the ring opening of epoxides by alcohols
D. Bradley G. Williams and Michelle Lawton
DOI: 10.1039/B508924G

Cyclizative radical carbonylations of azaenynes by TTMSS and hexanethiol leading to α-silyl- and thiomethylene lactams. Insights into the E/Z stereoselectivities
Mami Tojino, Noboru Otsuka, Takahide Fukuyama, Hiroshi Matsubara, Carl H. Schiesser, Hiroki Kuriyama, Hironari Miyazato, Satoshi Minakata, Mitsuo Komatsu and Ilhyong Ryu
DOI: 10.1039/B309944J

Photochemical intramolecular aromatic substitutions of the imidazol-2-yl radical are superior to those mediated by Bu3SnH
Mairéad A. Clyne and Fawaz Aldabbagh
DOI: 10.1039/B512729G

On the use of mixtures of organotin species for catalytic enantioselective ketone allylation—a detective story
Anthony Cunningham, Vijaya Mokal-Parekh, Claire Wilson and Simon Woodward
DOI: 10.1039/B313384B

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

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Chameleons and catalysis on the cover of the latest issue of OBC

The colourful images on our covers are from Andrew C. Benniston and Ming-Hua Xu et al.

Andrew Benniston (University of Newcastle) together with colleagues from Istanbul Technical University and Hacettepe University, Turkey have created a series of colour-responsive fluorescent fluorene-fused benzoquinones with potential for use as reactive oxygen species sensors.  One of the compounds synthesised exhibits ‘chameleon-like’ behaviour switching from red to blue fluorescence on reduction, and reverts back to red on reaction with ROSs.

Colour-responsive fluorescent oxy radical sensors
Baris Yucel, Bahar Sanli, Huseyin Akbulut, Suheyla Ozbey and Andrew C. Benniston
DOI: 10.1039/C2OB06825G

Ming-Hua Xu and colleagues at Shanghai Institute of Materia Medica have designed a structurally simple new class of chiral sulfur–olefin hybrid ligands – N-cinnamyl sulfinamides – for use in asymmetric catalysis. The ligands where tested in rhodium-catalyzed asymmetric 1,4-addition reactions, converting aryl boronic acids to α,β-unsaturated carbonyl compounds with up to 99% yield and 98% ee.

Design of N-cinnamyl sulfinamides as new sulfur-containing olefin ligands for asymmetric catalysis: achieving structural simplicity with a categorical linear framework
Shen-Shuang Jin, Hui Wang, Ting-Shun Zhu and Ming-Hua Xu
DOI: 10.1039/C2OB06723D

This issue also contains a review on the recognition properties of imidazole derivatives by Franscico Otón et al. and a hot article from Luis Simón and Jonathan Goodman on hydrogen-bond stabilization in oxyanion holes, showing that the 3D arrangement, rather than planar arrangement, of H-bonds stabilises oxyanion holes.

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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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Building a nation of scientists

Goverdhan Mehta talks to Sheena Elliott and Elinor Richards about the progress of science in India and the challenges scientists face

Goverdhan Mehta is a researcher, specialising in organic synthesis. He has helped to build institutions in India – the Indian Institute of Technology, Kanpur, the University of Hyderabad, and the Indian Institute of Science, Bangalore. He was director of the Indian Institute of Science (1998-2005) and vice chancellor of the University of Hyderabad (1994-1998).

Your research is focused on organic chemistry. What attracted you to that field?

There is something intrinsically fascinating about organic chemistry. In my early high school years, when I was exposed to interesting chemical structures, I was attracted to them. I had a sense of appreciation for art and organic molecules to me provided a wonderful expression of art at a molecular level.

What are your main achievements in the field?

I have worked in many areas of organic chemistry, but it’s synthesis that’s given me the greatest pleasure. As organic chemistry advanced, different contemporary challenges came to my attention. The main driver for me to pursue those challenges was the intricacy of the target structure synthesis. There was also an element of expectation that perhaps our research might become useful to society. We continue to need new drugs for a variety of disorders, so we synthesised a large number of natural products; many of them are biologically active and it is quite possible that some of them can provide leads for new drug discovery.

Over the last few years, I have become interested in how to address a problem that the ageing population is facing – neurodegeneration. It has been shown that some natural products can slow down neurodegeneration. In some cases, there is also an indication that they can help restore lost cognitive function. So I have been working on the synthesis of such lead molecules. As I’m getting older, I recognise the need for doing something in that area!

You’ve won numerous awards. Which achievements are you most proud of?

I don’t think that awards and recognition have necessarily brought me a great sense of joy. They do bring a sense of satisfaction because your peers have recognised your work. But I don’t think any serious researcher works for awards. It is the sheer joy of research that keeps people going. Recognition has come my way, but don’t think that I can equate that with the joy of doing research.

What are the challenges facing scientists in India and how could these be overcome?

Scientists all over the world are facing challenges on two fronts. The first problem is that scientists are not being supported by society as much as they should and some governments are not always forthcoming in terms of providing budgetary support. The second problem is that scientists, and science in general, have become isolated both in terms of discipline and, to some extent, in terms of geographical location. This is being redressed now with increasing international collaborations, so in the geographical sense, the isolation is being reduced. But I think disciplinary isolation vis a vis other knowledge streams and fragmentation of science is still a serious challenge.

It is a good time for scientists in India because the government is very supportive of science. Funding is no longer as serious a problem as it is in other parts of the world. Recently, our prime minister said that the budget for science will be almost doubled over the next few years. But I’m not too sure that we as a scientific community are steering science in India in the direction that it ought to be heading. I believe that the government and the scientific community must set a goal that in the next 10 years, India will be among the world’s leading scientific countries.

What is your opinion on the perception that Indian science and research is falling behind the rest of the world, following recent comments by Prime Minister Manmohan Singh?

Prime Minister Singh’s statement referred mainly to China. China has made more progress in science and technology than India. Scientific productivity in India has increased, but not as much as in China. Since we are behind, to simply say that we are walking and walking well is not enough. We should be galloping to catch up. My judgement is that our progress is not commensurate with the support that the government is providing, and not commensurate with the capacity, capability, enthusiasm and the vibrancy that our youth have. We can achieve much more.

How do the different industries compare (the pharmaceutical industry in particular or the more general chemical industry)?

It is only over the last 10 or 12 years, since the economic reforms, that industry in India has grown at such a rate so as to be in a position to invest in research and development. I expect that investment by industry is going to rise; however, the current level of investment is not in an acceptable range. There are certain sectors – pharma, for example – and some other chemical industries, where I think India’s potential is immense, but there are some challenges with the policies that are being pursued. We have to devise a well thought out strategy.

The prime minister’s Science Advisory Council reported that there in an absence of any Indian universities among the world’s best. What is your opinion on the quality of universities in India?

I’m not a great believer in the ranking systems being followed, but the fact is that no Indian university features among the top few hundred  universities. However, if we were to look at undergraduate teaching, India has institutions that produce graduates through excellent teaching and training. The graduates are probably as good as they are anywhere else in the world. If you were to grade an institution on the quality of undergraduates, I would say that the Indian Institutes of Technology rank among the top 10 institutions in the world. But, if you bring in research and other elements, they will not feature anywhere near the top. So the quality of research is a serious problem. I think it is high time that the scientific community and scientific leadership in our country sort out an effective, implementable strategy to make a major shift.

You experienced difficulty obtaining a visa to travel to the US in 2006, when you were invited to give a lecture at the University of Florida. At the time, a report from the National Academy of Sciences in the US said that at least 3000 scientists had faced a similar problem. Have things improved since then or do you believe that the visa problem is hampering scientific progress and career development for scientists?

It was ironic that I and a leading scientist from the US, Jane Lubchenco (who at that time was president of the International Council for Science before I succeeded her), wrote an editorial about the principle of universatility of science and the visa regime in Science a few months before this happened. We wrote that it was important for the international growth of science that scientists were able to travel. Little did I realise that soon I would be a victim of this! I think the situation has improved, but a lot more needs to be done. While the US National Academy of Sciences is playing a very positive role towards this end, the academies can only do the advocacy. Eventually, it is the government and the state department of security staff that makes the final judgement.

If you have any spare time, how do you fill it?

For most scientists, and I’m no exception, your research is a hobby. What other profession can give you that pleasure and privilege? In a previous interview, I was asked what I would wish for. I said we Indians believe in rebirth and so the only wish I have is that if I were to be born again, I would be a scientist. I would like to be a chemist, hopefully a better one.

Read some of Goverdhan Mehta’s recent research:

Towards a temperature-guided molecular switch: an unusual reversible low-temperature polymorphic phase transition in a conformationally locked environment
Goverdhan Mehta and Saikat Sen, Chem. Commun., 2009, 5981
DOI: 10.1039/b905651c

Understanding the self-assembling process in crystalline cyclooctitols: an insight into the conformational flexibility of medium-sized rings
Goverdhan Mehta, Saikat Sen and Kotapalli Pallavi, CrystEngComm, 2008, 10, 534
DOI: 10.1039/b712877k

Additive induced polymorphous behavior of a conformationally locked hexol
Goverdhan Mehta, Saikat Sen and Kailasam Venkatesan, CrystEngComm, 2007, 9, 144
DOI: 10.1039/b613949c

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Top 10 Emerging Area articles from Organic & Biomolecular Chemistry

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

Asymmetric organocatalysis
Jayasree Seayad and Benjamin List
DOI: 10.1039/B415217B

The golden gate to catalysis
Anja Hoffmann-Röder and Norbert Krause
DOI: 10.1039/B416516K

Organocatalysis: asymmetric cascade reactions catalysed by chiral secondary amines
Xinhong Yu and Wei Wang
DOI: 10.1039/B800245M

A hitchhiker’s guide to G-quadruplex ligands
David Monchaud and Marie-Paule Teulade-Fichou
DOI: 10.1039/B714772B

Advanced organic synthesis using microreactor technology
Batoul Ahmed-Omer, Johan C. Brandt and Thomas Wirth
DOI: 10.1039/B615072A

Diversity-oriented synthesis; a challenge for synthetic chemists
David R. Spring
DOI: 10.1039/B310752N

“Frustrated Lewis pairs”: a concept for new reactivity and catalysis
Douglas W. Stephan
DOI: 10.1039/B802575B

Synthesis of protein–polymer conjugates
Karina L. Heredia and Heather D. Maynard
DOI: 10.1039/B612355D

Catalytic asymmetric hydroamination of non-activated olefins
Kai C. Hultzsch
DOI: 10.1039/B418521H

Out of the oil bath and into the oven—microwave-assisted combinatorial chemistry heats up
Helen E. Blackwell
DOI: 10.1039/B301432K

Want to write a new emerging area that you think is going to be big in the future? Why not get in contact – we’d love to hear your ideas.

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Mouth bacteria makes metabolite that could prevent yeast infections

A bacteria present in the mouth – Streptococcus mutans – has been shown to generate the metabolite mutanobactin A by scientists from the US. They found that the metabolite inhibits biofilms formed by the fungal oral pathogen Candida albicans, which causes yeast infections.

In biofilms, pathogens are less susceptible to antibiotics, so this finding could have implications for treating yeast infections.

Fungal biofilm inhibitors from a human oral microbiome-derived bacterium
Xiaoru Wang, Lin Du, Jianlan You,  Jarrod B. King and Robert H. Cichewicz
DOI: 10.1039/C2OB06856G

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Multivalent scFvs, mitomycin C stereochemistry, peptide dendrimers and NET ligands in Issue 8

On the cover of Issue 8 we have two cancer-related articles from Jacquelyn Gervay-Hague (University of California Davis) on multivalent single chain variable fragments with increased tumor-associated antigen affinity and from Federico Gago (Universidad de Alcalá) modelling the binding of mitomycin C and analogues to DNA.

A general chemical synthesis platform for crosslinking multivalent single chain variable fragments
Joan G. Schellinger, Avinash Kudupudi, Arutselvan Natarajan, Wenjun Du, Sally J. DeNardo and Jacquelyn Gervay-Hague
DOI: 10.1039/C0OB01259A

Rationale for the opposite stereochemistry of the major monoadducts and interstrand crosslinks formed by mitomycin C and its decarbamoylated analogue at CpG steps in DNA and the effect of cytosine modification on reactivity
Juan A. Bueren-Calabuig, Ana Negri, Antonio Morreale and Federico Gago
DOI: 10.1039/C1OB06675G

The issue also contains a review from Jean-Louis Reymond and Tamis Darbre on combinatorial libraries of peptide and glycopeptide dendrimers and hot papers on creating (D)-sugars from (L)-amino acids from Paul Clarke and stilbazolium dimers as NET ligands from James N. Wilson.

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HOT article: (D)-sugars from (L)-amino acids – a step closer to understanding the origin of life

A conundrum for anyone studying the prebiotic world is how chirality first occurred, and why D-sugars are the natural isomers, whereas natural amino acids have the L-configuration. In this hot paper Paul Clarke and Christopher Hayes from the Universities of York and Nottingham have shown how carbohydrates could have formed in prebiotic conditions by producing (D)-erythrose and (D)-threose sugars with (L)-amino acid catalysts.

Having first used proline esters to catalyse the aldol reaction of TIPS-protected glycolaldehyde in water with good yields and moderate diastereo- and enantioselectivity, the group hypothesised that other proteinogenic amino acids (i.e. amino acids found in proteins) could also catalyse this reaction.  Using N-methyl derivatives of the amino acid esters of (L)-alanine, (L)-leucine and (L)-valine they were able to produce the expected sugars, but were surprised to see that the (D)-enantiomer was the major product in all reactions. “This offers one potential explanation to account for the relationship between (L)-amino acids and (D)-sugars in nature” concludes Clarke.

This remarkable find has obviously generated a lot of interest in both scientific and the wider press: see articles in The Daily Mail, The Huffington Post, on Science Daily or the press release from University of York.

Asymmetric organocatalytic formation of protected and unprotected tetroses under potentially prebiotic conditions
Laurence Burroughs, Paul A. Clarke, Henrietta Forinto, James A. R. Gilks, Christopher J. Hayes,  Matthew E. Vale , William Wade and Myriam Zbytniewski
DOI: 10.1039/C1OB06798B

This article is also part of our joint web theme issue with ChemComm on Organocatalysis and as with all our hot articles will be free to access for 4 weeks.

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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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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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