Organic & Biomolecular Chemistry Blog

Outstanding organocatalysis: An article collection

13 Jun 2012

A collection of high impact articles on organocatalysis from the RSC’s ChemComm, Catalysis Science & Technology Organic & Biomolecular Chemistry (OBC) and Chem Soc Rev.

Catalysts are key to some of the most important reactions on the planet; a world without the Haber process or catalysts to crack crude oil is difficult to imagine. Not to mention the enzymatic reactions that are crucial to all life on earth.

Organocatalysts are an important class of catalyst and consist of carbon-based molecules often functionalised with oxygen, sulfur, nitrogen or phosphorus. They have shown promise in a range of reactions including hydrogenation, Diels-Alder, Michael and Mannich reactions, and are of particular interest in asymmetric reactions.

To help keep you up-to-date with the latest in cutting-edge organocatalytic research we have made the following articles free to access until the 9th July. After reading all these there will be little you won’t know about the exciting world of organocatalysis!

Click here for the full list of free articles

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10 of the best: medicinal chemistry in Organic & Biomolecular Chemistry

12 Jun 2012

By James Anson.

Continuing our blog series celebrating OBC’s 10th anniversary we bring you a selection of 10 of our most highly cited articles in the area of medicinal chemistry. Every single one will be free to access for you to enjoy for the next week.

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

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

HIV-1 protease: mechanism and drug discovery
Ashraf Brik and Chi-Huey Wong
DOI: 10.1039/B208248A

Cell-penetrating peptides as delivery vehicles for biology and medicine
Kelly M. Stewart, Kristin L. Horton and Shana O. Kelley
DOI: 10.1039/B719950C

Novel molecular drug carrier: encapsulation of oxaliplatin in cucurbit[7]uril and its effects on stability and reactivity of the drug
Young Jin Jeon, Soo-Young Kim, Young Ho Ko, Shigeru Sakamoto, Kentaro Yamaguchi and Kimoon Kim
DOI: 10.1039/B504487A

Synthesis and evaluation of analogues of 10H-indolo[3,2-b]quinoline as G-quadruplex stabilising ligands and potential inhibitors of the enzyme telomerase
Bérangère Guyen, Christoph M. Schultes, Pascale Hazel, John Mann and Stephen Neidle
DOI: 10.1039/B316055F

Mechanism and structure–reactivity relationships for aromatic hydroxylation by cytochrome P450
Christine M. Bathelt, Lars Ridder, Adrian J. Mulholland and Jeremy N. Harvey
DOI: 10.1039/B410729B

The merger of natural product synthesis and medicinal chemistry: on the chemistry and chemical biology of epothilones
Karl-Heinz Altmann
DOI: 10.1039/B405839A

Two-stage enzyme mediated drug release from LMWG hydrogels
Kjeld J. C. van Bommel, Marc C. A. Stuart, Ben L. Feringa and Jan van Esch
DOI: 10.1039/B507157G

Designer aminoglycosides: the race to develop improved antibiotics and compounds for the treatment of human genetic diseases
Mariana Hainrichson, Igor Nudelman and Timor Baasov
DOI: 10.1039/B712690P

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

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Nanoscience: Regulating the traffic across cells membranes

11 Jun 2012

By Nathalie Horner.

Nanopore-forming materials have many potential applications in chemistry and biology, including DNA sequencing. However, only very limited designs of synthetic nanopores exist in the literature. US scientists have made circular molecules made of sugars that can stack on top of one another to form a transmembrane pore and act as carriers to shuttle the guest molecules across the membrane.

Hydrogen bond-assisted macrocyclic oligocholate transporters in lipid membranes
Lakmini Widanapathirana, Xueshu Li and Yan Zhao
DOI: 10.1039/C2OB25301A

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OBC issue 25 now online: featuring Yamada–Otani condensation & organocatalytic dendrimers

07 Jun 2012

By James Anson.

Welcome, dear reader, to issue 25 of OBC!

The front cover of this week’s issue highlights the work of Rich G. Carter, Oregon State University, and colleagues. In this paper Carter et al. present the development of a proline sulphonamide-catalysed method that facilitates the annulation of α-aryl, α-alkyl-disubstituted aldehydes with acyclic enones to produce highly functionalized cyclohexenones with very good degrees of diastereoselectivity and enantioselectivity.

Proline sulphonamide-catalysed Yamada–Otani condensation: reaction development, substrate scope and scaffold reactivity
Hua Yang, Somdev Banerjee and Rich G. Carter
DOI: 10.1039/C2OB25400J

The inside cover highlights the review of Brian Rasmussen and Jørn Bolstad Christensen that looks at the growing field of organocatalysis with dendrimers. This review outlines advances made in this area of organocatalysis and covers both interior- and surface-based examples, the catalysis of reactions ranging from functional group interconversion and C–C bond forming reactions to enzyme mimicking processes.

Organocatalytic dendrimers
Brian Rasmussen and Jørn Bolstad Christensen
DOI: 10.1039/C2OB25317H

Also featuring in this issue are several examples of our Organocatalysis web themed issue. Including the front cover article these are:

Asymmetric Michael addition of boronic acids to a γ-hydroxy-α,β-unsaturated aldehyde catalyzed by resin-supported peptide
DOI: 10.1039/C2OB25431J, Communication

Catalyst development for organocatalytic hydrosilylation of aromatic ketones and ketimines
DOI: 10.1039/C2OB25472G, Paper

Polystyrene-supported TBD catalyzed ring-opening of N-tosylaziridines with silylated
DOI: 10.1039/C2OB25435B, Paper

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Organic: Self-sorting compound mixtures

05 Jun 2012

By Nathalie Horner.

A judicious choice of precipitation conditions can lead to self-sorting of equilibrating mixtures of aromatic aldehydes and substituted anilines into a handful of imine products, say researchers from the US.

You might expect to get quite a few different products but because the least soluble imine precipitates, the mixture re-equilibrates to generate more of that compound. Eventually, all precursors to the least soluble imine are exhausted and the mixture is reduced in complexity. Only the most and the least soluble imines are produced without any of the “in between” species.

A mixture of as many as nine imines could be self-sorted into just three compounds, they say.

Precipitation-driven self-sorting of imines
Rio Carlo Lirag , Karolina Osowska and Ognjen Š. Miljanić
DOI: 10.1039/C2OB25736J

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10 of the best: catalysis in Organic & Biomolecular Chemistry

04 Jun 2012

By James Anson.

In this latest blog celebrating OBC’s 10th anniversary we bring to you a selection of 10 of the most highly cited articles that cover the area of catalysis. Every single one will be free to access for you to enjoy.

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

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

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

Organocatalysis with proline derivatives: improved catalysts for the asymmetric Mannich, nitro-Michael and aldol reactions
Alexander J. A. Cobb, David M. Shaw, Deborah A. Longbottom, Johan B. Gold and Steven V. Ley
DOI: 10.1039/B414742A

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

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

σ-Chelation-directed C–H functionalizations using Pd(II) and Cu(II) catalysts: regioselectivity, stereoselectivity and catalytic turnover
Jin-Quan Yu, Ramesh Giri and Xiao Chen
DOI: 10.1039/B611094K

Primary amino acids: privileged catalysts in enantioselective organocatalysis
Li-Wen Xu and Yixin Lu
DOI: 10.1039/B803116A

[2.2]Paracyclophane derivatives in asymmetric catalysis
Susan E. Gibson and Jamie D. Knight
DOI: 10.1039/B300717K

Do you remember these articles? Have they influenced your work? Share your comments below, we would love to read them.

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Chemical biology and medicine: New anti-cancer mechanism for drug compounds

01 Jun 2012

By Nathalie Horner.

Serbian chemists have synthesised a similar compound to the anti-cancer drug paclitaxel, but while this new compound is also bad news for cancer cells, the mechanism it uses is quite different – autophagy instead of apoptosis. Paclitaxel causes cancer cells to self destruct, but cancer can become wise to this and become resistant. The new analogue uses autophagy to kill the cancer – a method of attack that’s getting increasing attention for anti-cancer drugs.

A novel C,D-spirolactone analogue of paclitaxel: autophagy instead of apoptosis as a previously unknown mechanism of cytotoxic action for taxoids
Milena Trmcic, Radomir Matovic, Gordana Tovilovic, Biljana Ristic, Vladimir Trajkovic, Zorana Ferjancic and Radomir Nikola Saicic
DOI: 10.1039/C2OB25514F

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OBC issue 24 now available, featuring oligonucleotides and self-sorting on the covers

31 May 2012

By James Anson.

This week’s OBC front cover highlights the review of Sabine Müller and colleagues who discuss the methods for the preparation of oligonucleotides. In particular Müller et al. review the work done in the field of synthesis of trinucleotide synthons representing codons for the 20 canonical amino acids and their use for fully controlled partial or total randomization individually at any number of arbitrarily chosen codon positions of a given gene.

Mixed oligonucleotides for random mutagenesis: best way of making them
Tamil Selvi Arunachalam, Claudia Wichert, Bettina Appel and Sabine Müller
DOI: 10.1039/C2OB25328C

On the inside fron cover Manik Lal Saha and Michael Schmittel present a review on the emerging principles of how to guide several components toward the formation of self-sorted multi-component architectures, and in whcih they focus on developing a systematic classification for the reported self-sorting systems and an evaluation of their degree of self-sorting

Degree of molecular self-sorting in multicomponent systems
Manik Lal Saha and Michael Schmittel
DOI: 10.1039/C2OB25098E

Both of these reviews will be free to access for the next 6 weeks so get reading!

Also in this issue is the HOT communication by Marco Bella et al. regarding a modern take on the Rabe animation utilising organocatalyisis.

The Rabe amination after a century: direct addition of N-heterocycles to carbonyl compounds
Daniele M. Scarpino Schietroma, Mattia R. Monaco, Valerio Bucalossi, Philipp E. Walter, Patrizia Gentili and Marco Bella
DOI: 10.1039/C2OB25595B

View the whole issue here….

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HOT: The Rabe amination after a century: direct addition of N-heterocycles to carbonyl compounds

29 May 2012

By James Anson.

This Communication by Marco Bella et al. is a study of the historically famous Rabe amination, presenting preliminary results for a “modern” organocatalytic version of the reaction whereby direct functionalisation of ketones and aldehydes with N-chloro amines is achieved in mild conditions. Bella et al. also report that when aldehydes bearing a CH₂ moiety in the α-position are used, a novel rearrangement is observed leading to α-amino ketones.

Have a look at the Communication for more details on the experimental procedure and possible mechanistic explanation for this interesting reaction, it’s free to access for 4 weeks!

The Rabe amination after a century: direct addition of N-heterocycles to carbonyl compounds
Daniele M. Scarpino Schietroma, Mattia R. Monaco, Valerio Bucalossi, Philipp E. Walte, Patrizia Gentili and Marco Bella
DOI: 10.1039/C2OB25595B

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Organic & Biomolecular Chemistry Blog

Outstanding organocatalysis: An article collection

10 of the best: medicinal chemistry in Organic & Biomolecular Chemistry

Nanoscience: Regulating the traffic across cells membranes

OBC issue 25 now online: featuring Yamada–Otani condensation & organocatalytic dendrimers

Organic: Self-sorting compound mixtures

10 of the best: catalysis in Organic & Biomolecular Chemistry

Chemical biology and medicine: New anti-cancer mechanism for drug compounds

OBC issue 24 now available, featuring oligonucleotides and self-sorting on the covers

HOT: The Rabe amination after a century: direct addition of N-heterocycles to carbonyl compounds

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