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Mo and W MonoAryloxide-Pyrrolide (MAP) olefin metathesis catalysts can couple terminal olefins to give as high as >98% Z-products in moderate to high yields with as little as 0.2% catalyst. Results are reported for 1-hexene, 1-octene, allylbenzene, allyltrimethylsilane, methyl-10-undecenoate, methyl-9-decenoate, allylB(pinacolate), allylOBenzyl, allylNHTosyl, and allylNHPh. It is proposed that high Z-selectivity is achieved because a large aryloxide only allows metallacyclobutanes to form that contain adjacent cis substituents and because isomerization of Z-product to E-product can be slow in that same steric environment.
This publication is the first solution to the 50 year old problem concerned with Z-selective coupling of terminal olefins. |
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Professor JoAnne Stubbe receives 2010 Franklin Medal
Professor JoAnne Stubbe, Novartis Professor of Chemistry and Professor of Biology, has been selected to receive a 2010 Benjamin Franklin Medal in Chemistry for uncovering the intricate processes by which cells safely use free radicals, for developing new cancer treatments, and for improving the production of environmentally-friendly biodegradable polymers. For 185 years, The Franklin Institute has honored the greatest men and women of science, engineering, and technology. The Franklin Institute Awards are among the oldest and most prestigious comprehensive science awards in the world. Among science's highest honors, The Franklin Institute Awards identify individuals whose great innovation has benefited humanity, advanced science, launched new fields of inquiry, and deepened our understanding of the universe.
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| Joe Francisco |
Dick Schrock |
Tim Swager |
Paula Hammond |
K.Jones-Prather |
A.Chakraborty |
Cathy Drennan |
The NOBCChE NE Regional Meeting is being hosted by the MIT Departments of Chemistry and Chemical Engineering on Friday, October 23 and Saturday, October 24.
The meeting will open on Friday 3:00 PM at LeMeridien Hotel, 20 Sydney Street, Cambridge, with Professor Joseph S. Francisco, President-Elect of ACS and William E. Moore Distinguished Professor—Physical Chemistry, Purdue University, opening the session. Career planning guidance will be offered following Professor Francisco's talk, and MIT students and students from around the northeast region will be presenting posters.
Professor Richard R. Schrock, Frederick G. Keyes Professor of Chemistry, will be giving the opening talk on Saturday morning, and NOBCChE is very excited and appreciative to have a Nobel Laureate presenting. Professor Paula Hammond, Bayer Professor of Chemical Engineering, will be delivering the Plenary Lecture on Saturday afternoon. Professor Hammond is a founding member of the MIT NOBCChE chapter, and it is with great pride that NOBCChE welcomes her as the Plenary Lecturer!
Professor Timothy M. Swager, John D. MacArthur Professor of Chemistry and Head of the Department, and Professor Hammond will give a workshop on Careers in Chemistry for Graduate students. Professor Kristala Jones-Prather, Chemical Engineering Department and Professor Arup Chakraborty, Robert T. Haslam Professor of Chemical Engineering, Professor of Chemistry and Professor of Biological Engineering, will present a workshop on Applying to Graduate School for undergraduates on Saturday morning. Professor Catherine L. Drennan, Professor of Chemistry and Biology, and Investigator and Professor, Howard Hughes Medical Institute, will present a talk during the technical program. Technical talks are being given both in the morning and afternoon, and representatives from several companies will be available to chat with everyone about opportunities in their company. |
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PETER CURTIN
It is with great sadness that the Department reports on Saturday, Oct. 10, Chemistry Department graduate student Peter N. Curtin, passed away while running the Baltimore Marathon. Peter, a graduate student in inorganic chemistry, was in his second year in the research group of Daniel Nocera, the Henry Dreyfus Professor of Energy and Professor of Chemistry, and was recently selected to receive a National Defense Science and Engineering Graduate Fellowship. There will be a Memorial Service at the MIT Chapel on Thursday, October 22, 2009, at 3:30 p.m.
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Professor JoAnne Stubbe wins National Medal of Science
Professor JoAnne Stubbe, Novartis Professor of Chemistry and Professor of Biology, was presented the National Medal of Science by President Obama, at the White House, on Wednesday, October 7, 2009 at 1:30 PM.
Click here to watch the ceremony
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The Department of Chemistry is very pleased to host Professor John Harkless, Martin Luther King Visiting Professor, for the 2009-2010 academic year. An Associate Professor of Theoretical and Computational Chemistry at Howard University, his research focuses on three topics:
1) Quantum Monte Carlo wave function development
2) Electronic structure of metallic systems
3) Electronic excitations.
Professor Harkless is currently the Vice President of NOBCChE, the National Organization for the Professional Advancement of Black Chemists and Chemical Engineers.
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ACS 2010 National Award Winners
Four Chemistry Department professors have been selected to receive 2010 American Chemical Society National Awards:
Ronald Breslow Award for Achievement in Biomimetic Chemistry:
Professor Stephen J. Lippard
ACS Award in Colloid and Surface Chemistry:
Professor Moungi G. Bawendi
Elias J. Corey Award for Outstanding Original Contribution in Organic Synthesis by a Young Investigator:
Professor Mohammad Movassaghi
Arthur C. Cope Scholar Award:
Professor Alice Y. Ting
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"Formation of ArF from LPdAr(F): Catalytic Conversion of Aryl Triflates to Aryl Fluorides."
A new way to prepare fluorinated pharmaceuticals
--New method gives drug designers more flexibility
The Buchwald Group has devised a new way to add fluorine to a variety of compounds used in many drugs and agricultural chemicals, an advance that could offer more flexibility and potential cost-savings in designing new drugs.
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Silencing of tryptamine biosynthesis for production
of non-natural alkaloids in plant culture
Weerawat Runguphan, Justin J. Maresh and
Sarah E. O’Connor
online in PNAS, week of August 3, 2009
Here we show that RNA mediated suppression of tryptamine biosynthesis in Catharanthus roseus hairy root culture eliminates all production of monoterpene indole alkaloids. To exploit this chemically silent background, we introduced an unnatural tryptamine analog to the production media and demonstrated that the silenced plant culture could produce a variety of novel products derived from this unnatural starting substrate. Targeted suppression of substrate biosynthesis therefore appears to be a viable strategy for programming a plant alkaloid pathway to more effectively produce desirable unnatural products. |
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Emeritus Professor, Dietmar Seyferth, has been elected to the 2009 inaugural class of Fellows of the American Chemical Society.
When it meets next month in Washington, D.C., the society will honor its first class of ACS Fellows. These 162 members "share a common set of accomplishments, namely true excellence in their contributions to the chemical enterprise coupled with distinctive service to ACS or to the broader world of chemistry," says Immediate Past-President Bruce E. Bursten, who championed creation of the program and shepherded it through board approval last year.The 2009 ACS Fellows will be honored at a special ceremony during the ACS National Meeting in Washington, D.C. in August 2009. |
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Meiliana Tjandra and Dr. Jun Qi in the Movassaghi group have completed the
first total synthesis of (–)-himandrine.
Their synthesis features a diastereoselective Diels-Alder reaction in the rapid synthesis of the tricycle ABC-ring system in enantiomerically enriched form, the use of a formal [3+3] annulation strategy to secure the CDE-ring system with complete diastereoselection, and successful implementation of their biogenetically inspired oxidative spirocyclization of an advanced intermediate. The successful and direct late-stage formation of the spirofused BF-rings in the hexacyclic core of himandrine drew on the power of biogenetic considerations and fully utilized the inherent chemistry of a plausible biosynthetic intermediate.
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