musings on music and life

July 4, 2015


Filed under: Chemistry — Tags: , — sankirnam @ 12:30 pm

I got back from the NOS (National Organic Symposium) a few days ago, and am still recovering from the (slight) jetlag and that oh-so-familiar feeling one gets when they are living and breathing organic chemistry 24/7. The NOS is a biennial conference organized by the ACS Division of Organic Chemistry. I’ve wanted to go to this for a while, as the NOS has a rich history, and is the conference for organic chemists. Presenting here is considered far more prestigious (at least for organic chemists) than presenting at a national ACS conference. This year, it was held in the University of Maryland, College Park. The organizer was Prof. Marisa Kozlowski (UPenn), and she deserves full credit for organizing the event and making sure everything ran perfectly. I prefer attending these divisional symposia (such as the NOS and the Winter Fluorine Conference) because of the smaller size. This makes it easier to talk to people, as there is a higher chance you will run into them multiple times, and due to your common background, gives you a conversational ice-breaker (“so, which group do you work for?”, etc.), making networking infinitely easier. Plus, the lectures and chemistry being presented are top-notch as well!

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The NOS was preceded by the JOC editors’ symposium. This is also held every two years, and the last one was held at UC Irvine, and it was there that I rather incoherently babbled about chemistry for the whole world to see. The lecture in the photo above is by Prof. Olaf Wiest (Notre Dame Univ.) on his theoretical studies on Heck reactions.

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The art and practice of total synthesis is alive and well, judging by the quantity and quality of the posters in this session.

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The lectures were started off with a bang by Prof. D. W. C. MacMillan (popularly known as “DMac”). He is a brilliant presenter, and his unparalleled clarity of thought is evident not just in his approach to chemistry but also in the elegance and structure of his presentations. If people were afraid that the art of giving good organic chemistry lectures died with Prof. R. B. Woodward, fret not…

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This was followed by a lecture by Prof. Matthew Gaunt (Cambridge). He is most famous in my eyes for a rather interesting paper he published in Science in 2009 on meta-selective C-H arylation. While the reaction is unique and no doubt useful, the mechanism is still up for grabs. In this talk he presented methods for the synthesis of complex amines based on Pd-catalyzed C-H activation of bonds α or β to the nitrogen.

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Prof. Abigail Doyle (Princeton) then presented her work involving the combination of Ni catalysis and photoredox chemistry. This seemed to be the prevailing trend in the conference; Pd is out, Ni is in! And thanks to the advances in photoredox chemistry by MacMillan, C. R. J. Stephenson, Tehshik Yoon, and others, radical chemistry is making a comeback.

For those who don’t know, Abigail Doyle is particularly famous in organic chemistry circles because she got a tenure-track position at Princeton without having to do a postdoc! I emphasize that last statement because it is nearly unthinkable today; even industry positions are requiring a PhD and postdoctoral experience due to the oversaturation of PhD’s in the chemistry job market. It probably helped that Abigail did her PhD with Eric Jacobsen at Harvard; he has an excellent track record in placing his students at top academic institutions. I remember in my sophomore year at UCI (2005), the department hired 2 Jacobsen postdocs as tenure-track professors, Chris Vanderwal and Liz Jarvo.

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Shoutout to the Petasis reaction! This was developed by Prof. Nicos A. Petasis at USC; his hall and lab were very close to the one I worked in during my PhD.

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Prof. Kuiling Ding (Shanghai Institute of Organic Chemistry) gave a tour-de-force lecture on asymmetric catalysis. I had heard him talk before at USC several years ago, and this lecture was more or less on the same topic (asymmetric reactions with Ti-BINOL complexes). While the work he presented is not necessarily groundbreaking or novel, it is nonetheless tremendously important. He emphasized the fact that a lot of new reactions discovered in academia use unacceptably high catalyst loadings (1 mol % or more), and his work on high-throughput ligand screening enabled the development of new complexes for established reactions that are active even at loadings as low as 0.001 mol %; oftentimes, these would still maintain ee‘s > 95%! I’m sure Sharpless would be pleased, had he been present.

For those who don’t know, Kuiling Ding is the director of the SIOC, the premier chemistry research institute in China!

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Prof. Larry Overman (UCI) was the keynote speaker of this symposium, since the Division of Organic Chemistry had awarded him the Roger Adams Medal (the highest honor of the DOC) in 2015. Prof. Overman is one of the rockstars of natural products total synthesis, and has a number of synthetic methodological breakthroughs to his credit as well, including the eponymous Overman Rearrangement, the Aza-Cope-Mannich reaction, and asymmetric Heck reactions. As a UCI chemistry alum, it is pleasing to see UCI getting more and more recognition!

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Mark Ondari (Dow Chemical) talked about their work in the synthesis of donor/acceptor molecules for applications in OLEDs. This was fundamentally different from all the other talks in that the emphasis was not about discovering something new; the primary concern was the development of reliable, scalable synthetic routes to the desired molecules in very high (>99.99%) purity.

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Prof. Kenichiro Itami (Nagoya Univ.) gave a great talk as well. I was pleasantly surprised at his accent (or lack thereof)! He talked mainly about one reaction, the para-selective C-H functionalization of aromatics. However, it was impressive how he had managed to leverage that one reaction to branch out into all the fields mentioned in the slide above. Using that reaction, he was able to develop (in conjuction with Prof. Steve Kay at USC) new molecules for the disruption of circadian rhythms in cells. He also showed some extremely interesting work on the functionalization of corannulene and other polycyclic aromatics, work he dubbed “nanocarbon chemistry”. Rather unexpectedly, the credits slide of his presentation blew everyone away, and was probably the highlight of the conference!

EDIT (1/17/2017): Video of Itami’s talk! Check out the video from 57:40 onwards.

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Prof. Kendall Houk (UCLA) talked about his recent theoretical work in probing the intimate details of cycloadditions. He began by reminiscing about the past, mentioning that the first NOS he had attended featured a heated debate between Prof. H. C. Brown (Purdue) and Prof. Saul Winstein (UCLA) over the classical/nonclassical nature of the 2-norbornyl cation! This debate was moderated by Prof. G. A. Olah, and one should remember that this was the period when physical organic chemistry was extremely hot and carbocations were trendy.

Prof. Houk also talked about the development of computational chemistry, acknowledging the contributions of people like Kohn, J. A. Pople, M. J. S. Dewar, and Karplus, Levitt, and Warshel.

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Wendy Young (Genentech) gave one of the concluding talks of the conference, detailing some of the work towards synthesis of new drug candidates at Genentech. She did happen to mention that they had an opening for 1 (only!) medicinal chemist – I’m sure that they are now swamped with applications.

I’m sure the Divison of Organic Chemistry will upload the lectures for public viewing later; I’ll update this post with the links once I get them.

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