Talk:Organocatalysis

Conflict of Interest

The recent contributor, User:Mike Kotke, has made a large improvement to the page. All of the content looks very good, actually, but some wikification to meet our manual of style are needed.

HOWEVER, there appears to be a conflict of interest with regard to the citations. What I am saying, is that nine out of the fourteen specific references are to do with Peter R. Schreiner's group (see http://www.chemie.uni-giessen.de/home/schreiner/Alumni/ and http://www.chemie.uni-giessen.de/ma/liste/schreiner/). Perhaps some balance is needed. --Rifleman 82 02:36, 31 May 2007 (UTC)

Rifleman 82; thanks for your comments and interest on organocatalysis. I removed the web-link to our homepage. With regard to the citations, please note, below the images I cite several articles of other groups and contributors to the field of non-covalent organocatalysis, so the development of this research field should become clear. It can not be avoided that any author or group might be considered underrepresented. That is a problem well-known in the scientific community. User:Mike Kotke

I don't do organocatalysis, so I do not follow the development of this field. However, I do believe that organocatalysis is more than simply noncovalent organocatalysts. Those other aspects should be expanded on, and the article should not dwell on this sub-field only. Unless there are good reasons. Perhaps this is the only sub-field giving good progress for example? --Rifleman 82 14:53, 31 May 2007 (UTC)

Allow me to just interject. Firstly, the grammar was somewhat simplistic and required some clean-up and other things. There are problems generally with the article at the moment because the images aren't really explaining much to those who don't understand this topic. I've read up on organocatalysis for about 7 years, but still. Firstly, the image section at the bottom needs to be broken up, and split into paragraphs which explain the other forms of catalysis because on their own, the images don't really add much other than an illustration, and so need to be changed.

Secondly, the large image isn't even needed. Rather than have a fancy green image listing journals that were used, it'd be much easier to simply explain the development of organocatalysis methods and commercial uses over the years with in-line references than have a somewhat difficult-to-read image that just lists some journal entries.

Thirdly, the references need trimming down now or the article needs to expand -- a large amount of them have no relevance to the article, so we obviously must expand. In future, please be careful as to the terminology that's used in explanations, as simplification is a good idea, BUT if overdone can leave a fragmented and tangential approach.

Nevertheless, thanks for the contributions and please follow the Wikipedia: Manual of Style ♥♥ ΜÏΠЄSΓRΘΠ€ ♥♥ ^{slurp me!} 16:20, 31 May 2007 (UTC)

I don't think this is a serious conflict-of-interest problem. The article is over-referenced for its length, yes, we don't have enough discussion as to the mechanism of organocatalysis, no. I hope that Mike Kotke can help us on these points (because I can't!). Physchim62 (talk) 16:35, 31 May 2007 (UTC)

I've done enough around the topic to be able to expand it easily at any rate. Give me a few days, i have a few large projects ready to go at the moment, and a lot of work to mark in the next week. ♥♥ ΜÏΠЄSΓRΘΠ€ ♥♥ ^{slurp me!} 16:37, 31 May 2007 (UTC)

Dear all, I've been working in the field of non-covalent organocatalysis for several years, theoretically and experimentally. To date there are more than 600 publications on organocatalysis (if you see the restart in 2000, much more when considering historical aspects) and 130 articles are on non-covalent organocatalysis utilizing hydrogen bonding. The historical background goes back to Liebig's time and continues at the beginning of the 20th century.

Recently, I prepared a manuscript for a book-chapter on hydrogen-bonding organocatalysis with a special look at thiourea derivatives. For this reason I gave some information to wikipedia. Otherwise I would not have invested my time to do so. Wikipedia will never give an entire overview on this rapidly growing research field and you can always be of the opinion that a image or a reference is not necessary or something is missing. This is the same when reading an scientific article on any topic of natural science. There are in each case reasons for discussions. Wikipedia will never replace any scientific article, this can not be the goal. But wikipedia can inform someone, who is not familiar with a topic and make him look up original literature for further information and studies. This has been my goal, namely to give a reader a spectrum of information. Just 4 weeks ago, no wikipedian seemed to be interested in organocatalysis (not even ΜÏΠЄSΓRΘΠ€), although it has been already an important field for several years.

Looking up organocatalysis in wikipedia 4 weeks ago you had found just 5 sentences explaining that this field uses purely organic compounds. Now, I expand it and all of a sudden there is interest and everyone seem to give clever comments on style, on images, on references, what's important or not and so forth. Dear wikipedians, you can believe me, it's quite plain to me, that my entries do not represent the entire spectrum of organocatalysis, covalent organocatalysts are missing (e.g., proline!) , e.g., hydrogen-bonding amidinium salts, ADDOLS, BINOLS and PHANOLS are missing, PTC, peptides and more, but my entries gave an overview on noncovalent hydrogen-bonding through thioureas, review articles are cited, and the outstanding importance of the bis-3,5-CF3-phenyl group found by Schreiner is explained and scientifically affirmed by citations. So, dear ΜÏΠЄSΓRΘΠ€ and others, it's not a wild selection of some journals, the green image underlines the central meaning of this organocatalyst and the reader can rapidly see, what kind of organic reactions can be catalyzed. Wikipedia is not the place for presentations and discussions on mechanisms. This would be to much information.

So, if someone wants to get first information on noncovalent organocatalysis by using wikipedia, now this person can find much more than 4 week ago. By the way, it will be hard to find commercial uses of organocatalysts. As I know from several confernces, indstustry to date is more or less not interested in organocatalytic processes. To my knowledge in Japan a Maruoka PTC-catalyst is used in a large-scale application, not more. There is, of course, MacMillan's catalyst that you can purchase from Aldrich, but Wikipedia should not be the platform for advertisement. But if there is one, who wants to add this catalyst to wikipedia, he should feel free. I will not be this person. Finally, please excuse my mistakes in wikipedia's style and, of course note, I'm also able to expand wikipedia's organocatalysis at any rate - but what for? I started the entries - and you don't, that's the fact. Note: I removed my E-Mail address I've once added here, as it is not longer active. Thanks.

Best regards, M. Kotke

Mr Kotke, you misunderstand me. I didn't assert that you had added random journal entries -- I had to verify the information that you added, and have come to the conclusion that they are all correct and relevant, but also that they are too much in number, and placed improperly. For instance, the large image, whilst all the references on it are completely relevant to the topic, they aren't relevant to the article as they don't actually "reference" anything. In the Wikipedia, the general policy is that references are performed in-line with the text so they are easily verifiable for another reader or editor is passing by. This isn't much of a difference between other forms of university-referencing, as there's quite a few out there, particularly journals which use the same mark-up style.

I was not suggesting that you were incorrect or going against what you had added, but rather the way in which you had added it; my field of chemistry and major isn't this area, so I'd be somewhat of a second fiddle to someone such as yourself, who is. The reason, again is .. when there are larger images in the middle of the page, generally they have to be very descriptive. Although the image in the middle is lovely, and the journals around it relevant as a focal point, comparison or what have you, it's basically a list of journals (which are completely relevant to the topic, i must stress), that don't illustrate anything more than "there's a rapid amount of expansion in this field".

While it's a good indication to the number and relevancy of journals, we have to take on board others, aside from chemists who read these articles and assume that they come to them as a laymen, willing to take advantage of this information that we have provided for them, regardless of their field of endeavour. Please don't take this as an indication as an attack on you, your work or anything else, it's just a suggestion made in the realms of Wikipedia policy; we want information to be viewable and accessible to all walks of life. Please don't feel that you must add information simply for your own sake, but rather because it's being made available to everyone, which is the actual reason I choose to edit here, and hope you'll come to also. ♥♥ ΜÏΠЄSΓRΘΠ€ ♥♥ ^{slurp me!} 18:31, 31 May 2007 (UTC)

I agree with Mike, organocatalysis is a big topic that has been neglected by Wiki. We should be glad to have a specialist taking an interest in this topic even if it means the content gives prominence to one particular branch in this field. it is simply up to others to complete the picture. Compare this article to the Aldol reaction article also mainly written by a specialist and now a featured article thanks to the combined effort of the Aldol specialist and many wiki specialists. V8rik 18:50, 31 May 2007 (UTC)

How is this in disagreement? I stayed away from the "how much can we expand on this topic" and went for the cleanup and relevancy. I can guarantee you that there are thousands of pages on the wikipedia related to rapidly expanding topics that aren't anywhere near the frontier of discovery because there aren't enough people willing to add the information in themselves! This isn't anything new, though! ♥♥ ΜÏΠЄSΓRΘΠ€ ♥♥ ^{slurp me!} 18:57, 31 May 2007 (UTC)

Thanks again for your interest in organocatalysis and in the stuff I added to wikipedia. Thanks for the helpful comments and the nice changes in style so that the article becomes more and more attractive. Nevertheless, there seems to be rather differnt opinions concerning the wikipedia style, e.g., the style of the citations was already changed three times by different persons. So, I see the problem, too many cooks spoil the broth. It's hard to find a compromise and make everyone feel good on this article; if I prepare the article for a layman, so the expert could say, that's not correct, too easy, or not complete. In the other way round, the layman could complain about many references, the complicate structures of any mechanism and so forth. I higly estimate the engagement and experience you have in wikipedia and many users profit. I confess, I have no experiences in wikipedia and I'm not willing to become a wiki-expert, but I do have experiences in the field of organocatalysis (and of course other persons using wikipedia). So, we could benefit from each other: Since I prepare a scientific book-chapter on organocatalysis, I have to be informed on the historical background and the latest developments in organocatalysis and have to prepare many details for this manuscript. The deal could be, in the next days, weeks and month I will add step by step (note, the article is still growing and not finished at all) more deatails, structures, references, images,....to improve this wiki article (everyone is, of course invited to do so). Your job, if you not want to add information, could be the improvement of my style in the way some of you has already done. This is my suggestion to form together a nice article. But, if we did not find a common strategy, I think it would be better to me spending my time in my research and somebody of the "cooks" may cook the soup. Think about it. Regards, Mike Kotke

Mhm. I don't mean to sound like a shirker, but I tend to just do things rather than talk about how rapidly developing they are; an article that is as up-to-date as we can get is fine by me, and of course, thanks for your contributions. You don't have to be a wiki-expert; we try to aim for a medium between the expert, the laymen and the intermediary. In every other place i've worked, it's been the exact same when mathematicians, chemists and physicists work together; a camel is a horse designed by committee in any situation, so there's no real way of saying "i'll struggle writing something which everyone will be happy with", because there's always one person who will complain about it because that's the way humans are. ♥♥ ΜÏΠЄSΓRΘΠ€ ♥♥ ^{slurp me!} 14:49, 1 June 2007 (UTC)

• Once again I refer to the Aldol reaction article:
  • the bulk of the article was written by a specialist and when he started did have like you limited knowledge of Wiki
  • major issues to solve were citations!. Citation are annoying to edit but the only correct style is by inline referencing and ideally with DOIs. In the Aldol article others simply helped out and I think others can help you out in this article too (I will volunteer).
  • Another issue: translating the topic to laypeople!, other people besides the specialist helped constructing the introduction where things are explained on a more basic level. Others helped with internal linking
  • with respect to conflict of interest the specialist works in the Evans group and I count Evans name 26 times in the article. Some bias there?

So nothing new here really (this is how articles evolve), I really suggest you continue your edits and I for one will offer assistance. We will go for featured article status and nothing less

Having said that two issues remain:

• citations should really be relevant to the text (Wiki is not a deposit of citations)
• The article will be helped with more general information and less specialist information

V8rik 19:47, 1 June 2007 (UTC)

Now this is the thing, V8rik. I've tried to fix the references into the inline style which is recommended. But, out of the fourteen "specific" references, I only see 1, 2, 6, 8. Either I'm not staring hard enough or they simply aren't there, and should be dropped or listed elsewhere. --Rifleman 82 02:47, 2 June 2007 (UTC)

Is it possible to talk here about organocatalysis without giving any reference of Barbas III, MacMillan or even List. I think it isn't but I see it is. —Preceding unsigned comment added by 157.88.40.223 (talk) 18:25, 6 September 2007 (UTC)

• It is clear from the discussion above that what happened here is that the article is skewed towards thioureas. Ideally the article should have started out as a general article on organocatalysis followed by additions covering specific topics (MacMillan is there though). The article is in need of somebody to write a general piece. V8rik 19:28, 6 September 2007 (UTC)

References

I've turned most of the references into the standardized {{cite journal}} style including dois in place of urls. Would appreciate it if anyone can help turn them into <ref> style. --Rifleman 82 06:57, 1 June 2007 (UTC)

Proline-catalysed aldol

The Aldol reaction article has a nice section and a diagram for the proline-catalysed aldol and the Hajos-Parrish ketone. Should it be copied directly into this article? A link from here to Aldol reaction seems to be diverting the reader unnecessarily......

Let me copy and paste here the corrected text from another site of Wikipedia. Please consider it here to satisfy the history of Organocatalysis and to have the text and the picture in agreement.The rest is self-explanatory.Zghajos (talk) 09:14, 9 March 2008 (UTC)

"Discovered in the 1970's the original Hajos-Parrish catalytic procedure shown in the reaction equation leading to the optically active bicyclic ketol as well as the Eder-Sauer-Wiechert modification leading to the optically active dione paved the way of asymmetric organocatalysis.

Hajos and Parrish worked at ambient temperature using a catalytic amount (3% molar equiv.) of (S)-(-)-proline enabling them to isolate the optically active intermediate bicyclic ketol. The Schering group used non biological conditions using (S)-Proline (47 mol%), 1N perchloric acid, in acetonitrile at 80 °C. Hence, they could not isolate the Hajos, Parrish intermediate bicyclic ketols but instead the condensation product."

concerning the removed picture "thiourea - overview"

Dear all, if anybody is ere, wo can give me a sensible reason for removal of the overview-picture on the standard thiourea catalyst that is described in the text? I don't see any. This picture was created by me, all references were cited correctly, and the reader was informed on the outstanding capabilities of this thiourea in the field of organocatalysis. To my opinion this removal means a large loss of information for this aticle. Finally, I must repeat a statement I already gave above: No-one before was interested to give the rapidly growing field of organocatalysis a platform in wikipedia. I did start to do so, and some guys think, they must act as referees. And what do you think to know better? For what? To remove scientifically correct information to the readers of this article? If this seems to be the tendency and the wish of some arrogant so-called scientists it's just a waste of time to me contributing anything. Please remember, it's always much easier to criticize but it's even harder to do it better. To date, nobody did it better (apart from the changing the formatting). MK.

The images you had uploaded had a copyright problem - on one hand you gave a free license template; on the other hand you said it was only for use on wikipedia. In particular:

“ All images on Wikipedia must comply with the image use policy. This means that they must be compatible with the conditions of the GNU Free Documentation License. In particular, images must be free for commercial use and alteration. Some fair use of copyrighted material is, however, allowed in limited circumstances. ”

Do note that fair use images are being actively removed from wikipedia, as far as is possible, so the latter clause does not hold much water anymore. If you wish to upload an image under a free license, such as GFDL or PD-self, that would be perfectly acceptable under wikipedia rules. --Rifleman 82 16:43, 5 July 2007 (UTC)

• I agree with Rifleman, if the licence tag is incorrect the image will be removed. If you reupload the image with a GFDL licence there will be no problem. We have already discussed the other issue: the current article is heavy on the thioureas and if you are able to add some content about organocatalysis in general it will only improve the article. V8rik 17:11, 5 July 2007 (UTC)

So I added the thiourea picture with a GFDL license. MK