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29 January 2009 15,981 views 36 Comments

It really is time that someone took the crayons away from KCN – the covers of the Classics books are bad enough without this crazy colouring-in competition turning up in JACS abstracts

Also of note – nice work by Carreira in Nature today; this’ll be in my RSC Chemistry World column.

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  • synthesis says:

    woot. another synthesis in Nature.

  • Jetset says:

    Well said tot. syn. – has anyone actually told him that these kaleidoscope rings are better suited to childrens books than science papers?

  • sjb says:

    Presumably you mean March’s Chem World, rather than February’s?

  • aa says:

    i’m not asking this in any kind of accusing way, but i believe i remember MacMillan presenting an intramolecular alpha arylation of aldehydes at the ACS meeting in Philadelphia. does anyone else recall this, or know how this paper impacts MacMillan’s work?

  • The Next Phil Baran says:

    If we want to push to get them to stop making pretty diagrams, and thereby inflating their work, then we have to be equally critical of the use of “novel”, or “biological activity”, etc. The biological activity of a molecule does not matter to a synthetic chemist, nor does its uniqueness. The mere act of describing its biological activity is simply a restatement of the cinctures of public money on the organic chemist. “I received money for this project because I lied to the government by saying it was about the greater good” = “this molecule has shown strong activity against…………..”

  • milkshake says:

    This asymmetric ring-forming reaction is instantly useful to medicinal chemists – he earned his right to use these horrible colors.

  • HPCC says:

    Sorry, kids, but there’s a graphic designer in KCN’s office whose job is, more or less, to “KCN-ize the figures”, i.e. add the colours and make the structures nice and homogeneous.

    Blame her on your next seizure… :P

  • InfMP says:

    This isn’t the typical design work of his. Usually he has everything warped all over the place, like a dream. Phil Baran has apparently picked up the same artist.

    This color scheme is used for structures in KCN’s “Molecules that changed the world,’ a wonderful book with some really great pictures and stories (even though it emphasizes his own work).

    I would really like to draw like this; I am going to ask Andre Charette the next time I see him, since it’s similar to his schemes in the Nature intro for Trost Bryostatin

  • inorganic refugee says:

    @ The Next Phil Baran

    JACS outlawed the use of the word “novel” in titles a few years ago. IIRC.

  • Stephen says:

    How fast will a chiral center flanked by an aldehyde and aromatic ring racemize? It seems like the slightest basic or acidic condition will do this, which might limit any applications of this methodology.

  • milkshake says:

    The best thing is to oxidize or reduce the product right away – a common situation in organocat.

  • ee says:

    Who cares if its KCN’s graphic designer’s falt! As the man in charge, KCN should be responsible for what his group publishes. I mean lots of PI’s have their students write the paper, but that doesn’t mean they let it get published with bogus statements, grammar errors, etc. Including these colorful rings in a scientific manuscript is silly, even if it is only the abstract.

  • WestCoast85 says:

    Is there a mistake in the first scheme ? It’s a radical cation and no a radical anion… Shame on Nicolaou !!!

  • The Next Phil Baran says:

    Yes they did stop the use of novel, however, they did allow other adjectives and superlatives to remain. What about: interestingly, surprisingly (as though their is some predictive power in their possession), or even efficient? We are not English majors or novelist and therefore we shouldn’t be allowed to embellish work with descriptive terms that are not in the material but are interpretations of the observer. I can understand having colored schemes for clarity, ie to emphasize a certain part of the molecule that undergoes change, but to emphasize the entire molecule is counter-productive.

  • matt says:

    Wow, what a face lift.

  • The one says:

    Thats the best look that this blog ever had. Good job !

  • Pilky01 says:

    WestCoast85, I agree I think it should be a radical cation if you lose an electron (especially as it combines with electron rich aryl appendages)

    To be clear from the start I have no affiliation with KCN, but I actually like the coloured schemes and stuff. Nobody said that publications couldnt be asthetically pleasing aswell as scientific. I also like this blog which has been recently redesigned (good job Tot.Syn.) to deliver scientific discussion in a more artistic manner. Sure, its not publishing the latest ground breaking chemistry but still its a semi-proffesional arena of science. Is it really a big deal that someone who is supposed to be creative and innovative is doing his job.

    Again, i agree with InfMP: The molecules book is really excellent but it does oversell his work a bit too much, The straw that broke my back (im not a camel!) and made me smile at his shameless self pronounced prowess (which is partly warranted) was the molecule in a little box on the spine of the book!!

    Lastly, I’d like to meet David Sarlah and discuss chemistry with him, he seems to be doing pretty well.

  • ch3mical says:

    Pilky01 says:

    WestCoast85, I agree I think it should be a radical cation if you lose an electron (especially as it combines with electron rich aryl appendages)

    The cation is represented in the later scheme, which makes it more of an error in the beginning

    • alkaloid says:

      There is nothing new about this transformation except the catalyst he is using. Gaunt (U of Cambridge) has reported the same series of molecules using hypervalent iodine and a proline-based catalyst over a year ago. Should this have been in JACS?

  • 9-BBN says:


    Did Gaunt publish ahlpa-arylation? I thought it was all dearomatization… Very different products if you look at them…


  • new says:

    The catalyst is not new…check Aldrich, it’s listed under MacMillan. Unbelievable, what a rip-off!

    • Liquidcarbon says:

      As if someone said it was new…

      • new says:

        Alkaloid, 2 posts above my first.

        That is not the most important thing though. I think that the chemistry is great and the products are very useful but it was an obvious extension of methodology that another group has been pioneering. I have had discussions with both my advisor and lab-mates about this paper, and we all came to the same conclusion. Does anyone else think that there is something off about about this paper

  • rotavap says:

    Actually I cannot see many similarities in the work of Gaunt and KC’s work now … same series of molecules? … hypervalent iodine? And how many groups are using a proline-based catalyst for their research, precisely in organocatalysis!?

    Of course the catalyst is commercially available … try it out, it really does work fantastic for many kinds of transformations.
    But don’t you think that this is also wanted by MacMillan? … to introduce his catalyst so that many other groups will use it for their own purpose? He will always be mentioned in the references! And as KC permanently needs new and modern methodology to synthesize his molecules it is also understandable that he tries out some extensions from time to time. And hey, look at the series of molecules … I think they are very useful for a broad series of building blocks and biologically active molecules…

    And finally some last words about the colored molecules. I think KC does this for two reasons: First of all, I guess meanwhile he sees it as a kind of trademark for his manuscripts, talks and books … and second, everyone takes note of his work immediately from just scrolling down the webpage!!! I think there are worse ways to sell one’s work!

  • pasupathy says:

    off shoot topic: Can anybody suggest wether electrophilic reductions using borane complexes or alanes including DIBAL could be run in solvents other than THF OR DME or Toluene or DCM. My substrate is not soluble in any of the solvents as it contains a quaternary amonium salt. Your suggestion in this regard is highly appreciated.

    • Tot. Syn. says:

      You could try dioxane… but I’m not optimistic. At a push, perhaps basic methanol, or something like a borohydride-methanol system.

    • pasupathy says:

      Thanks for your suggestions. My substrate is not soluble either in dioxane. I am afraid to use nucleophilic reagents like NaBH4 as they resulted in undesired product. Probably I should try making a more organic soluble quaternary salt as suggested by ch3mical.

  • ch3mical says:


    or exchange your ammonium salt anion for something more organic soluble like hexaflourophosphate.

  • LW says:

    look the man is a dinosaur in his field. he makes these bloody molecules with so much ease (ok his students and post docs) its scary. let him use every colour in the rainbow, he’s earnt the right to. i’m just suprised he hasn’t given anyone an epileptic fit during a talk yet.

    @pasupathy– is your compound soluble in water? borane-amine complexes (i think) are compatible in aqueouss media

    • pasupathy says:

      thx dude. Already considered the option. But I have an acetal in the molecule. I am afraid because boranes are known to cleave them. Is temp a crucial factor in the cleavage of acetals.

  • Martyn says:

    Nicolaou’s given two more total syntheses the crayola treatment in Angewandte. Shame, they’re otherwise quite nice pieces of work.

  • Tot. Syn. says:

    Yep, I’ve got a post on BE-43472B brewing just now; should have it finished this evening. It might be a little longer before I’ve done sporolide B too… probably Sunday. Some damn nice stuff in there too. Also worth a look is EJ’s review on “Enantioselective Catalysis Based on Cationic Oxazaborolidines”.

  • ddd says:

    omg, somebody take away the crayons from this guy: http://pubs.acs.org/doi/abs/10.1021/jo900077j

    KCN’s colouring schemes literally pale in comparison..