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E N O A E S S S L T A E A C R C I th N S M A 90 Anniversary Issue of The NUCLEUS S E E H C C TI N April 2012 Vol. XC, No. 8 O CA N • AMERI
Monthly Meeting Summer Scholar Report 2012 Esselen Award Meeting at Harvard Regioselective Hydroformylation of Nosyl-protected Esselen Award to Professor Bruce Ganem Homoallylic Sulfonamides Ka H. Cheng and Kian L. Tan, Boston College HepatoChem April Historical Events An Interview of HepatoChem President, Marc Bazin in Chemistry By Leopold May, Catholic University of America Synthetic Liver Metabolites An interview with HepatoChem President, Marc Bazin By Michael P. Filosa HepatoChem (http:// (Fig 3). www.hepatochem.com/) HepatoChem has also partnered with Princeton-based is a company co-found - Novatia, http://www.enovatia.com/, a capillary NMR con- ed in 2008 by Marc tract laboratory, to do structure elucidation of metabolites Bazin, formerly of with small amounts of material (0.1-0.5 mg). Pfizer, and Professor Although only a four-person company at this stage, John T. Groves, holder HepatoChem already has numerous clients ranging from of the Hugh Stott Taylor start-ups to big Pharma. “Our clients are very satisfied with Chair of Chemistry at the quality and speed of our service.” Dr. Bazin stated that Princeton University. the business in liver metabolites is $100 million per year HepatoChem was started and their business is expected to grow rapidly for a number in the Groves lab at of years. “This is very exciting to see our company growing Princeton, but in August in this economy.” u 2011 moved to the Biotech InnoVenture Center in Beverly, MA. President Marc Bazin (r) and Project My interest in Hepa- manager Ryan Buzdygon photographed toChem was piqued by in HepatoChem’s Beverly laboratory. Business Development Manager Shelly Amster at a recent NESACS Monthly Meeting. A subsequent interview was arranged with HepatoChem President, Marc Bazin, at their Beverly facility. HepatoChem uses technology based on many years of metalloporphyrin research conducted at Princeton in the Groves laboratory. A variety of metalloporphyrins (Fig. 1) Fig. 1: A Synthetic Metalloporphyrin are used to simulate liver metabolism and oxidatively con- vert drug candidates in vitro to metabolites in milligram to gram quantities. This is in stark contrast to the nanogram quantities available by in vitro or in vivo biological methods. Easy access to large quantities of metabolites allows struc- ture determination and additional evaluation and testing, which would not be possible without the larger quantities available from HepatoChem’s biomimetic methods. “The technology we developed at HepatoChem can produce not Fig. 2. Graphical illustration of metabolites formed by the only metabolites but also new analogues of lead candidates oxidation of aminopyrine with HepatoChem’s technology. that could have better biological properties than the original drug. This positions it as an important tool for drug discov- ery.” Initial screening is done in 96-well plates loaded with the test molecule. A series of test reactions are then con- ducted in which the metalloporphyrin, the oxidant, and the solvent are varied. These experiments are then analyzed by Fig. 3: Metabolites formed by biomimetic oxidation of LC-MSMS to identify a profile of metabolites and allows Tolbutamide. rapid selection of conditions to produce the targeted metabolite. (Fig 2) A second round of experiments allows optimization and larger scale production of any or all of the metabolites generated in the screen. Your one-stop source to career-related links Examples of reactions which can be achieved with met- in the Chemical Sciences alloporphyrin oxidation are hydroxylation, imine and enam- ine formation, halogenation, carbene insertion, amine WWW.NESACS.ORG/CAREERS formation and dealkylation. Tolbutamide is an example which illustrates aliphatic hydroxylation and dealkylation
2 The Nucleus April 2012 The Northeastern Section of the American Chemical Society, Inc. Contents NESACS Office Anna Singer, 12 Corcoran Road, Burlington, MA 01803 Synthetic Liver Metabolites 2 (Voice or FAX) 781-272-1966. ______e-mail: secretary(at)nesacs.org An Interview of HepatoChem President Marc Bazin http://www.NESACS.org By Michael P. Filosa Officers 2012 Chair April Historical Events in Chemistry 4 Ruth Tanner ______Olney Hall 415B By Leopold May, Catholic University of America Lowell, MA 01854 University of Mass Lowell Ruth_Tanner(at)uml.edu Monthly Meeting ______5 978-934-3662 Esselen Award Meeting at Harvard University Chair-Elect Esselen Award to Professor Bruce Ganem, Cornell University Liming Shao Sunovion Pharmaceuticals Inc. Address: Lost (Sometimes) in Translation: Advancing Chemical Discoveries 84 Waterford Drive Beyond the Laboratory Marlborough, MA 01752 lshao(at)fas.harvard.edu Immediate Past Chair Announcements ______6,7 Patrick M. Gordon New England Association of Chemistry Teachers (NEACT), Central 1 Brae Circle Division Meeting. Lyman C. Newell Grants for the 73rd NEACT Woburn, MA 01801 Patrick.gordon65(at)gmail.com Summer Conference. NSYCC Northeast Student Research Conference, Secretary: NESACS Evening at a Red Sox Game Michael Singer Sigma-Aldrich 3 Strathmore Rd, Natick, MA 01360 NESACS Candidates for 2012 Election ______7 774-290-1391, michael.singer(at)sial.com Treasurer: Summer Scholar Report 8 James Piper ______19 Mill Rd, Harvard, MA 01451 Regioselective Hydroformylation of Nosyl-protected Homoallylic Sulfonamide. 978-456-3155, piper28(at)attglobal.net Ka H. Cheng and Kian L. Tan, Department of Chemistry, Boston College. Auditor: Anthony Rosner Announcement 11 Archivist ______Tim Frigo Chemistry of Food Science Café at Think Tank Bistrotheque, Trustees: One Kendall Square, Cambridge, MA Peter C. Meltzer, Esther A. H. Hopkins, Michael E. Strem Directors-at-Large Cover: 2012 Esselen Award winner Professor Bruce Ganem. (Photo courtesy David Harris, Stephen Lantos, James Phillips, of Professor Ganem). Ralph Scannell, Alfred Viola, John Burke Councilors Alternate Councilors Deadlines: Summer 2012 Issue: June 15, 2012 Term Ends 12/31/2012 Amy E. Tapper Jerry P. Jasinski September 2012 Issue: July 15, 2012 Catherine E. Costello Gary R. Weisman Patricia A. Mabrouk Norton P. Peet Dorothy J. Phillips Edward J. Brush Ruth Tanner Michael Hurrey th Term Ends 12/31/2013 90 Anniversary Issue of The NUCLEUS Thomas R. Gilbert Alfred Viola The Nucleus is published monthly, except June and August, by the Northeastern Section of the American Michael Singer Sophia R. Su Chemical Society, Inc. Forms close for advertising on the 1st of the month of the preceding issue. Text Robert Lichter Kenneth C. Mattes must be received by the editor six weeks before the date of issue. Mary Shultz Tim Frigo Leland L. Johnson, Jr. Raj (SB) Rajur Editor: Michael P. Filosa, Ph.D., ZINK Imaging, Inc., 16 Crosby Drive, Building 4G, Term Ends 12/31/2014 Bedford, MA 01730 Email: Michael.filosa(at)zink.com; Tel: 508-843-9070 Katherine Lee Michaeline Chen Associate Editors: Myron S. Simon, 20 Somerset Rd., W. Newton, MA 02465, Tel: 617-332-5273, Michael P. Filosa C. Jaworek-Lopes Sheila E Rodman, Konarka Technologies, Inc., 116 John St. Suite 12, Lowell, Doris Lewis Jennifer Larese MA 01852 Email: srodman(at)konarka.com tel 978-569-1414, Morton Z. Hoffman Lawrence Scott Mindy Levine, 516-697-9688, mindy.levine(at)gmail.com Patrick Gordon Marietta Schwartz Mary Burgess Andrew Scholte Board of Publications: Mary Mahaney (Chair), Mindy Levine, Vivian K. Walworth Business Manager: Karen Piper, 19 Mill Rd., Harvard, MA 01451, Tel: 978-456-8622 All Chairs of standing Advertising Manager: Vincent J. Gale, P.O. Box 1150, Marshfield, MA 02050, Committees, the editor Email: Manager-vincegale(at)mboservices.net; Tel: 781-837-0424 of THE NUCLEUS, and Contributing Editors: Morton Hoffman, Feature Editor; Dennis Sardella, Book Reviews the Trustees of Section Calendar Coordinator: Sheila Rodman, email: srodman(at)konarka.com Funds are members of the Photographers: Morton Z. Hoffman and James Phillips Board of Directors. Any Coun cilor of the American Chemical Soci- Proofreaders: Donald O. Rickter, Vivian K. Walworth, Mindy Levine ety residing within the section area is an ex Webmaster: Roy Hagen officio member of the Board of Directors. Copyright 2012, Northeastern Section of the American Chemical Society, Inc. The Nucleus April 2012 3 April Historical Events In Corporate Patrons $2000 - or more AstraZeneca Pharmaceuticals Chemistry Eisai Pharmaceuticals Leopold May, The Catholic University of America, Washington, DC 20064 EMD Serono Genzyme Corp. April 4, 1867 acids and their significance for in - Johnson Matthey A pioneer in clinical chemistry, Otto formation transfer in living material. Merck & Co. Folin, was born on this day. He April 10, 1790 Novartis engaged in the systematic develop- The U. S. Patent Office was estab- Pfizer Inc. ment of “micromethods”; the use of lished on this date according to Arti- Schering Corp. colorimetry in biochemistry using cle 8, Section 1 of the Constitution. Strem Chemicals, Inc. the Duboscq colorimeter; and the The first patent was granted to Vertex Pharmaceuticals use of an enzyme for analytical pur- Samuel Hopkins on potash and pearl $1000-$1999 poses: urease to measure urea. With ash. Boehringer Ingelheim Vintila Ciocalteu, he developed the GlaxoSmithKline “Phenol Reagent” for use in protein April 10, 1887 Irix Pharmaceuticals analysis. That is the basis of the One hundred and twenty-five years Lyophilization Services of NE Lowry method for protein determi- ago, Bernardo A. Houssay was born. Sundia Meditech nation. He received the Nobel Prize in Yes Bank Physiology or Medicine in 1947 $300-$999 April 6, 1928 with Gerty T. Cori and Carl F. Cori Cambridge Major Labs James D. Watson, born on this date, for their research on the hormone of conducted research on the double Girindus the anterior pituitary lobe and its Merrimack Consultants helix structure of DNA. Fifty years role in the metabolism of sugar. ago, in 1962, he shared the Nobel Organix Prize in Physiology or Medicine April 16, 1850 PCI Synthesis with F.H.C. Crick and M.H.F. Wil - Sidney G. Thomas, who solved the Sigma Aldrich kins for their discoveries concerning problem of separating phosphorus Waters Corp. the molecular structure of nucleic from iron in the Bessemer Con- Wilmington PharmaTech verter, was born on this date. April 17, 1869 Robert Robertson did research in explosives, including amato and tetryl (trinitrophenylmethyl- nitramine). He was born on this date. April 19, 1912 Glenn T. Seaborg was born on this date. He co-discovered americium (Am, 95) in 1944, berkelium (Bk, 97) in 1950, californium (Cf, 98) in 1950, curium (Cm, 96) in 1944, ein- steinium (Es, 99) in 1952, fermium (Fm, 100) in 1953, mendelevium (Md, 101) in 1955, nobelium (No, 102) in 1958, plutonium (Pu, 94) in 1940, and seaborgium (Sg, 106) in 1974. In 1951, he and Edwin M. McMillan received the Nobel Prize in Chemis try for their discoveries in the chemistry of the transuranium elements. April 20, 1912 Gertrude E. Perlmann was born on continued on page 12
4 The Nucleus April 2012 Biography Monthly Meeting Bruce Ganem is the Franz and Elisa- The 923rd Meeting of the Northeastern Section of the American beth Roessler Professor of Chemistry Chemical Society and Stephen H. Weiss Presidential Fel- low at Cornell. He graduated from Esselen Award Meeting Harvard College in 1969 with a B.A. in Thursday, April 19, 2012 Chemistry, and received his Ph.D. from Columbia University in 1972 under the Harvard University, Cambridge, MA direction of Gilbert Stork. He joined Harvard Faculty Club, 20 Quincy Street the Cornell faculty in 1974, where he has served as Chairman of the Depart- 5:30 pm Social Hour ment of Chemistry & Chemical Biol- 6:30 pm Dinner ogy from 1993 to 1997 and in 2001. A synthetic organic chemist by 8:15 pm Award Meeting, Mallinckrodt Building, 12 Oxford Street training, Dr. Ganem has broad scien- Pfizer Lecture Hall (MB23), Ground Floor tific research interests across the inter- Dr. Ruth Tanner, NESACS Chair, presiding faces of organic, analytical, and biological chemistry. His synthetic Welcome – Dr. Howard Mayne, Chair, Esselen Award Committee and mechanistic studies of the shikimic The Esselen Award – Dr. Myron S. Simon, Founding Member of the acid pathway helped elucidate how Esselen Award Committee plants and micro-organisms biosynthe- Introduction of the Award Recipient - Dr. Jon Clardy, Hsien Wu and size aromatic amino acids, vitamins, Daisy Yen Wu Professor, Department of Biological Chemistry and hormones, and other essential nutri- Molecular Pharmacology, Harvard Medical School. ents. Dr. Ganem has also developed new synthetic methods for assembling Presentation of the Award - Gustavus J. Esselen, IV naturally-occurring polyamines. His Lost (Sometimes) in Translation: Advancing Chemical Discoveries work in carbohydrate chemistry has Beyond the Laboratory - Dr. Bruce Ganem, Franz and Elisabeth focused on the synthesis and therapeu- Roessler Professor, and Stephen H. Weiss Presidential Fellow in the tic uses of saccharide analogs (glycol- Department of Chemistry and Chemical Biology, Cornell University. mimetics) as biological mediators. In the area of bioanalytical chem- Dinner reservations should be made no later than noon, Friday, April 13. istry, Dr. Ganem showed for the first Reservations are to be made using PayPal: http://acssymposium.com/ time that enzyme-substrate, receptor- paypal.html. Select pay with credit or debit card option and follow the addi- ligand and other noncovalent macro- tional instructions on the page. Members, $30; Non-members, $35; Retirees, molecular complexes could be detected $20; Students, $10. Reservations for new members and for additional informa- and analyzed by electrospray mass tion, contact the secretary Anna Singer at (781)272-1966 between 9am and spectrometry under physiological con- 9pm or e-mail at [email protected]. Reservations not cancelled at least 24 ditions. A principal focus of his cur- hours in advance must be paid. rent research is the development of THE PUBLIC IS INVITED new multiple component condensation Free Parking in the Broadway Street Garage (3rd level or higher), enter from reactions for use in combinatorial Cambridge Street via Felton Street. Directions to the Harvard Faculty Club can chemistry. be found at http://www.hfc.harvard.edu/ . Professor Ganem has authored some 250 scientific papers as well as numerous popular articles about sci- front individual chemical researchers ence and science education. He has Abstract seeking to translate chemical discover- been a consultant and advisory board ies into products and services for the member for several pharmaceutical The pursuit of academic chemical public good. Specific examples research is usually driven by the search and biotechnology companies. He selected from the awardee’s interdisci- served as Executive Editor of Tetrahe- for new knowledge and understanding plinary chemical research program about fundamental chemical dron Letters during 1998-2012, and over nearly forty years at Cornell will was appointed Chairman of the Execu- processes. From time to time such be presented to illustrate some of those research uncovers findings that can tive Board of Editors of Tetrahedron challenges and how (where possible) Publications during 2005-2006. His directly enhance the public welfare in they were surmounted. u some way. Several challenges con- Continued on page 12
The Nucleus April 2012 5 Announcements: New England Association of Lyman C. Newell Grants returning to teaching, the awards are Chemistry Teachers 73rd NEACT Summer open to all secondary school chemistry Central Division Meeting Conference teachers. Applicants need not be mem- bers of the Northeastern Section of the Saturday, May 12, 2012 Theme: Advances in Green American Chemical Society or of NEACT. Apply to NEACT directly. Gustaf H. Carlson School of Chemistry Chemistry Please contact Kathy Siok
THE COMMITTEE ON CHEMICAL ABSTRACTS (CCAS) WANTS YOUR FEEDBACK Visit our page on ACS Network: https://communities.acs.org/groups/ chemical-abstracts-service-committee or contact Michael Filosa with any suggestions at [email protected]
6 The Nucleus April 2012 NESACS Northeast Join NESACS Candidates Student for an evening with the for 2012 Chemistry Boston Red Chair-Elect Wilton Virgo Research Sox!!! Steve Lantos Friday, May 4, 2012 Cathy Costello Conference game starts at 7:10 pm Treasurer Jim Piper April 28, 2012 Boston Red Sox Auditor The 14th Annual NSCRC will be vs. Baltimore Orioles Anthony L. Rosner held at Northeastern University’s Trustee Curry Student Center Only $35 per ticket - includes handling charges Peter Meltzer Presented by the Northeastern Sec- Councilor/Alternate Councilor tion Younger Chemists Committee Reserve your tickets today by sending a check to: Norton P. Peet For more details go to our website at NESACS Raj (SB) Rajur NSYCC.org u Andrew Scholte Anna Singer Jennifer Larese 12 Corcoran Road Michaeline Chen Join NESACS Burlington, MA 01803 Dorothy J. Phillips Email [email protected] for Ruth Tanner on facebook additional information u Marietta Schwartz www.facebook.com/nesacs Heidi Teng Randy A. Weintraub Jackie O’Neil Mukund Chorghade Stuart Levy Kenneth Mattes Wilton Virgo Steve Lantos Cathy Costello Jerry P. Jasinski Norris Award Patricia Mabrouk Jerry P. Jasinski Patrick Gordon Directors-at-Large Al Viola James Phillips Nominating Committee Michael Filosa Jenny Li Petition Candidates: “Any group comprising 2 per cent or more of the members of the Northeastern Section (136 members) may nominate candi- dates…” See NESACS website for details. u
The Nucleus April 2012 7 Summer Scholar Report Regioselective Hydroformylation of Nosyl-Protected Homoallylic Sulfonamides Ka H. Cheng and Kian L. Tan, Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, United States Introduction: Hydroformylation, first discovered by Otto covalent binding of various organic functionalities, includ- Roelen in 1938, involves the addition of carbon monoxide ing both the substrate and the product, which enables the and hydrogen gas to an olefin to produce aldehydes. Nine catalytic usage of the ligand. The metal binding domain million tons of aldehyde products are produced per year by facilitates the coordination of the metal catalyst. The rhodium-catalyzed hydroformylation on an industrial scalei. entropic cost in bringing together both the substrate and the It is significant in commodity chemical synthesis because metal catalyst is used to accelerate subsequent hydroformyla- the aldehyde products are easily reduced to alcohols, which tionv (Figure 3). With the scaffolding ligand in hand, the Tan can then be converted to detergent or esterified to yield plas- group was able to control regioselectivity (branched-selec- ticizers. Rhodium–catalyzed hydroformylation is also tive) and enhance the reactivity such that less activated and applied to the synthesis of a key intermediate of vitamin Aii. trisubstituted olefins react under mild conditionsvi. The Tan Much effort has been put forth in studying hydroformylation group has also modified their original racemic ligand and due to its industrial significance. produced an enantioenriched ligand, which demonstrated good yield and enantioselectivity (up to 93% ee) in obtain- ing β-amino-alcohols from PMP protected allylic aminesi. The application of the scaffolding ligand to regioselec- tive hydroformylation of nosyl-protected homoallylic sul- fonamides is discussed in this report. Figure 1: Regiochemistry in Hydroformylation There are two primary challenges associated with regioselective hydroformylation. The first is the control of regioselectivity so that only the desired regioisomer is formed (linear or branched product). Given its industrial importance, academic and industrial efforts have been long focused in the development of catalysts for linear selective hydroformylation of terminal olefins.iii Branched- selective hydroformylation is often limited to activated substrates like styrene and vinyl acetate. The control of regioselectivity in Figure 2: Racemic Scaffolding Ligand hydroformylation is traditionally exerted via the use of stoi- chiometric phosphorus-based directing groups within the structure of the substrate. Although phosphorus-based directing groups are excellent ligands for the metal catalysts employed in hydroformylation, these functionalities have limited use in subsequent chemical transformations. Easily cleavable phosphorus-based directing groups have been developed to partially address this problem, but come with the inevitable shortcomings of additional synthetic steps and production of a stoichiometric amount of phosphorus-based byproductsi. The second challenge involves the optimization of the catalyst system to allow substituted olefins (often more sterically hindered) to be employed under mild reac- tion conditions Ouriv group and the Breitiii group simultaneously and Figure 3: Mechanism of the Scaffolding Ligand independently developed different phosphorus-based ligands Results: Three substrates (2, 3, and 4) were synthesized by in 2008 to address the above challenges. The concept of uti- utilizing the two routes shown in Figure 4. Although the lizing reversible covalent bonds to induce an intramolecular Mitsunobu reaction provides a one-step synthesis to the reaction is central to the development of our scaffolding desired substrates, the yields are low. The second route is phosphorus ligand. Our scaffolding ligand has both a sub- preferred because it gives a total yield of 79%, despite the strate binding domain and a metal binding domain (Figure fact that it involves two additional steps. Once the three sub- 2). The substrate binding domain allows for the reversible strates were prepared, the exchange of each of the three sub-
8 The Nucleus April 2012 strates on to ligand 1 was studied. To our surprise, the sul- summarized in Table 3, entries 1-5. It was found that vary- fonamide exchange occurred rapidly with ligand 1, with ing pressure does not produce any significant change to the exchange between 72 % and 81% (Table 1) in two hours, conversion, regioselectivity, and yield of the reaction. under moderate heating at 65 oC in the presence of a cat- Hydroformylation of substrates 3 using ligand 1 shows alytic amount of p-TsOH. excellent regioselectivity, good conversion and yield. The scaffolding ligand is able to direct the formation of branched isomer over the linear isomer with a 95:5 regioselectivity, compared to the almost 50:50 mixture exhibited by the triphenylphosphine control experiment (Table 2, entry 2). A pressure screen was performed and the results are summarized in Table 2, entries 6-10. It was observed that varying pressure does not produce any significant change in the conversion, regioselectivity, and yield, consistent with the results of the pressure screen of substrate 2. An acid concentration screen (Table 3, entries 11-15) was also performed, which showed that altering the concen- tration of p-TsOH does not improve the results. In fact, at 0.25% p-TsOH, the conversion begins to drop, potentially due to accelerated ligand decomposition. Substrate 4 was used in the hydroformylation reactions in entries 16 and 17. It should be noted that substrate 3 (with the trans-olefin) and Figure 4: Synthetic Routes for Substrates 2-4: two different substrate 4 (with the cis-olefin) behave similarly in hydro- routes are shown for the synthesis of substrate 3 formylation. An increase of rhodium catalyst loading from 2% to 4% (Table 3, entries 16-17) does not exhibit any sig- nificant change in the conversion, regioselectivity and yield. Conclusion: In summary, this research has focused on achieving excellent regioselectivity in the hydroformylation of homoallylic sulfonamides by using a phosphine-based scaffolding ligand designed by the Tan group. A model sys- tem was chosen, and pressure, rhodium catalyst loading, and acid concentration were screened. It was found that good conversion (>60%) and excellent regioselectivities (95:5) were achieved under mild conditions for substrates which Table 1: Exchange Data of Substrates 2, 3, and 4 with Scaf- Continued on page 10 folding Ligand 1 Hydroformylation reactions of substrates 2-4 were then investigated. As a control reaction, triphenylphosphine was used as the ligand, rather than ligand 1. The mixture of alde- hyde products after hydroformylation was oxidized and cyclized to the corresponding five-membered and the six- membered cyclic lactams. Substrate 2 (Table 2, entry 1) shows strong preference for the formation of the linear product over the branched product (B: L= 28:72), given that the terminal carbon is much more active. Hydroformylation of substrates 3 and 4(Table 2, entries 2 and 3) give almost 50:50 mixtures of the linear and the branched product, consistent with there being no discrimination between either disubstituted olefinic car- Table 2: Control Experiments of Substrates 2, 3, and 4 with bon by triphenylphosphine. Triphenylphosphine. Regioselectivity determined by 1H Hydroformylation of substrate 2 using ligand 1 shows a NMR. remarkable reversal in regioselectivity. Terminal olefin sub- strate 2 favors the formation of a linear product when triph- enylphosphine serves as the ligand. (Table 2, entry 1) The scaffolding ligand is able to overturn the regioselectivity to 60:40 in the favor of the branched isomer. Scheme 1: General Conditions of Hydroformylation Reac- A pressure screen was performed and the results are tions in Table 3
The Nucleus April 2012 9 Summer Scholar continued from page 9 are typically unreactive. Present work is focusing on expan ding the substrate scope, as well as the exploration of new enantio-enriched ligands to achieve high levels of enantioselectivity. Acknowledgement: KC gratefully acknowledges the ACS James Flack Norris/Theodore Williams Summer Research Scholarship for support of this work. References i Worthy, A.D.; Joe, C.L.; Lightburn, T.E.; Tan, K.L. J. Am. Chem. Soc. 2010, 132, 14757-14759 ii Chansarkar, R. Kelkar, A.A. Chaud- hari, R.V. Ind. Eng. Chem. Res. Table 3: Optimization of Homoallylic Sulfonamide Hydroformylation. Substrates 2009, 48, 9479–9489 2, 3, and 4 were exchanged with ligand 1 at 65oC prior to hydroformylation. Gen- iii Grünanger, C. U.; Breit, B. Angew. eral conditions of the hydroformylation reactions in entries 1-17 follow the ones Chem., Int. Ed. 2008, 47, 7346. given in scheme 1, except for the altered condition. Conversion, regioselectivity, iv Lightburn, T. E.; Dombrowski, M. and product yield were determined by 1H NMR. T.; Tan, K. L. J. Am. Chem. Soc. 2008, 130, 9210. The NESACS website v Tan, K.L. ACS Catal. 2011, 1, 877- 886 Updated frequently • Late-breaking news • position postings vi Lightburn, T. E.; de Paolis, O. A.; Back issues of the Nucleus archived • Career-related Links • Awards and Scholarships Cheng, K. H.; Tan, K. L. Org. Lett. WWW NESACS 2011, 13, 2686 – 2689. u . .org
10 The Nucleus April 2012 Chemistry of Food Science Café
Sara Risch Principal in the consulting firm Science By Design, which she founded in 1993. Sara works with food and packaging companies as well as those in related industries. Her talk will be focused on the chemistry of food and drink.
Geared toward adult festival attendees, this Science Café will be an engaging exploration of the everyday chemistry used in cooking.
Monday, April 23 Starts at 6:30 pm
Think Tank Bistrotheque One Kendall Square Building 300 Lower Level Cambridge, MA.
Free Hors d ’Ouvre’s and Drink RSVP
The Nucleus April 2012 11 February Biography Historical Events continued from page 5 continued from page 4 recent honors include the American this date. She did research in pro- Monthly Chemical Society’s 2007 Creative tein chemistry and received the Gar- Invention Award as well as the van Medal in 1965. EPA’s 2007 Presidential Green Chem- April 20, 1927 Meeting u istry Challenge Award. Born on this date, K. Alexander Photo by Morton Z. Hoffman Müller shared the Nobel Prize in Physics with J. Georg Bednorz in 1987 for their important break- through in the discovery of super- Join conductivity in ceramic materials. April 21, 1889 NESACS Eighty-five years ago in 1927, Paul Karrer shared the Nobel Prize in on facebook Chemistry for his investigations on carotenoids, flavins and vitamins A www.facebook.com/nesacs and B2 with Walter N. Haworth for Haworth’s investigations on carbo- hydrates and vitamin C. He synthe- (l-r) Liming Shao (Sunovion Pharmaceuticals), sized vitamins A in 1931, B2 NESACS Chair-elect; Ruth Tanner (University (riboflavin), in 1935, and E (toco- of Massachusetts Lowell), NESACS Chair; pherol) in 1938. He was born on this Craig Ferris (Northeastern University), speaker: Functional MRI in Awake Animals: date. Imaging the Neural Circuitry and Pharmacolog- April 22, 1919 ical Control of Aggression, Sex, and Fear. Twenty-five years ago in 1987, Don- ald J. Cram, born on this date, shared the Nobel Prize in Chemistry with C. J. Pedersen and J-M. P. Lehn for their development and use of molecules with structure-specific interactions of high selectivity. He did research in the application of stereochemical techniques to organic reaction mechanisms; invented carceplexes or guest mole- cules completely encapsulated by the host, and synthesized a variety of host-guest complexes including crown ether complexes. April 28, 1937 Seventy-five years ago, Champion International was incorporated on this date. Additional historical events can be found at Dr. May’s website, http://fac- ulty.cua.edu/may/Chemistrycalendar.ht m u
What exactly goes on at NESACS’ monthly Board meetings? www.nesacs.org/reports
12 The Nucleus April 2012 Calendar day-Saturday, October 23-26, 2013, From the at the Omni Hotel in New Haven, continued from page 16 CT. The host will be the New Haven Apr 24 continued NESACS Local Section. A website for the Prof. David S. Ginger (Univ. Washington) meeting will be developed in due Recombination Losses, Morphology, and course. Performance Limits in Organic and Hybrid Board BAGIM: K. Mattes Solar Cells MIT, 6-120 • The first 2012 Comp Together- 4:30 pm Minutes BAGIM meeting was held at the Ele- Prof. Daniel Kahne (Harvard Univ.) phant Walk Restaurant in Cambridge, Tufts, Pearson Chemistry Building, P-106 National Chemistry Week: MA. Meeting announcements were 4:30 pm C. Jaworek-Lopes made on the BAGIM Website Organic Syntheses Distinguished Lecture • NESACS will be partnering with the (http://www.BAGIM.org) , the Series Prof. Rich Carter (Oregon State Univ.) Museum of Science-Boston to hold NESACS Website (http://www. UNH, Room N104 (L103) an Earth Day event on Sunday, April nesacs.org/) and the Computer in 11:10 am 22, 2012 from 12-4 pm. Individuals Chemistry CompTogether website Apr 25 from Beyond Benign, Emmanuel (http://www.acscomp.org/COMP_To Prof. Philip Power (U. California, Davis) College, Northeastern University, and gether/) Harvard University, Pfizer Lecture Hall Salem State will participate in the • Nineteen (19) accepted the invitation 4:15 pm event. Each participating group will and twenty-one (21) attendees were Apr 26 bring an activity related to the theme present, representing 11 companies Prof. Jianmin Gao (Boston College) of Rethinking Recycling. and one university (Boston College). Tufts, Pearson Chemistry Building, P-106 • Jayashree Ranga from Salem State is Total cost for the food, including tip, 4:30 pm serving as an Earth Day co-coordina- was $828.70. Income for the dinner Madeleine Jacobs, Executive Director and tor. was $575.00 resulting in a net meet- CEO (American Chemical Society) Innovation, Chemistry, and Jobs • An email blast has been sent to local ing cost of $253.70. u UNH, Room N104 (L103) area teachers and Girl Scouts regard- 11:10 am ing the Chemists Celebrate Earth Day Boehringer-Ingelheim Lecture in Organic National Poem Contest. This infor- Chemistry mation will also be published in the Prof. Vy Dong (Univ. Toronto) MIT, 6-120 March Nucleus and on the NESACS 4:00pm website. Apr 27 NERM: M. Hoffman O’Malley Lecturer • NERM 2012 will meet on Sunday- Prof. Eric Kool (Stanford Univ.) Boston College, Merkert 130 Wednesday, September 30-October 3, 4:00 PM 2012, at the Radisson Hotel Riverside Apr 30 in Rochester, NY; see
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The Nucleus April 2012 15 Harvard, MA 01451 19 Mill Road
Prof. Kara Bren (Univ. Rochester) Prof. Matthew Platz (NSF Division of Multiple Structures and Multiple Functions of Chemistry) Cytochrome c: The Role of Covalently Bound Ultrafast Time Resolved Studies of Excited Heme States and Reactive Intermediates UNH, Room N104 (L103) U. Mass Lowell, Alumni Library 11:10 am 2:00 p.m. Prof. Carl Hoff (University of Miami) Apr. 16 Tufts, Pearson Chemistry Building, P-106 Prof. Ken Dill (SUNY, Stonybrook) 4:30 pm How do protein and proteomes govern the Apr 05 properties of cells? Prof. Simon North (Texas A & M) Brandeis, Gerstenzang 122 UNH, Room N104 (L103) 4:00 pm 11:10 am Apr 17 Kistiakowsky Lecture Prof. Abigail Doyle (Princeton Univ.) Prof. Paul Alivisatos (U. California, Berkeley) Boston College, Merkert 130 Harvard, Pfizer Hall 4:00 PM 5:00pm Prof. Janusz Pawliszyn (University of Waterloo) Apr 10 Tufts, Pearson Chemistry Building, P-106 Prof. Kelly J. Gaffney (Stanford Univ.) 4:30 pm Resolving the Mechanism of H-Bond Switching Prof. John Magyar (Barnard College) and Ligand Exchange in Aqueous Ionic Solution UNH, Room N104 (L103) AMERICAN CHEMICAL MIT, 6-120 11:10 am U.S. POSTAGE PAID NONPROFIT ORG. NORTHEASTERN 4:30pm SOCIETY SECTION Prof. Liming Zhang (U. California, Santa Apr 18 Barbara) University Lecturer Accessing alpha-Oxo/Imino Gold Carbenes via Prof. Charles M. Lieber (Harvard Univ.) Gold-Catalyzed Alkyne Oxidation: A Non-Diazo Whither Nanotechnology? Approach Boston College, Merkert 127 Boston College, Merkert 130 4:00 - 5:00 PM 4:00 PM Prof. Jeremy Smith (New Mexico State Univ.) Prof. Robert Bergman (U. California, Berkeley) Harvard University, Pfizer Lecture Hall UNH, Room N104 (L103) 4:15 pm Calendar 11:10 am Apr 19 Prof. David Moore (Lehigh Univ.) University Lecturer Check the NESACS home page Tufts, Pearson Chemistry Building, P-106 Prof. Charles M. Lieber (Harvard Univ.) for late Calendar additions: 4:30 pm Nanowires: From Synthesis to Energy http://www.NESACS.org Apr 11 Applications Note also the Chemistry Department web Boston College, Merkert 127 Prof. Apryll Stalcup (U. Cincinnati) 4:00 pm pages for travel directions and updates. What we learned about Chromatography from These include: Surface-confined Ionic Liquid Stationary Phases Prof. Sharon Hammes-Schiffer (Pennsylvania http://chemserv.bc.edu/seminar.html Northeastern University,129 Hurtig Hall State Univ.) http://www.bu.edu/chemistry/events/ 12:00 pm Proton-Coupled Electron Transfer in Catalysis http://www.chem.brandeis.edu/colloquium.shtml and Energy Conversion Prof. Shane Telfer (Massey University, New http://www-chem.harvard.edu/events/ MIT, 4-270 Zealand) http://web.mit.edu/chemistry/ 5:00 pm Creating Nothing Out of Something: www.chem.neu.edu/web/calendar/index.html Thermolabile Groups in Metal-Organic Merck-Karl Pfister Lectures in Organic http://chem.tufts.edu/seminars.html [CHEM.] Frameworks (MOFs) Chemistry http://ase.tufts.edu/chemical/seminar.htm MIT, 6-120 Prof. Craig J. Hawker (U. California, Santa [CHEM. ENGG.] 4:15 pm Barbara) http://www.chem.umb.edu/ MIT, 6-120 www.umassd.edu/cas/chemistry/seminars.cfm Apr 12 4:00 pm www.uml.edu/Dept/Chemistry/speakers.html Prof. Jeremiah Johnson (MIT) Iddles Lecture Series http://www.unh.edu/chemistry/seminars.html Looking for Loops in Polymeric Materials Prof. Weihong Tan (U. Florida) Apr 02 U. Mass Lowell Olney 218 UNH, Room N104 (L103) 3:00 p.m Prof. Sunny Zhou (Northeastern Univ.) 11:10 am Brandeis, Gerstenzang 122 Prof. Gonghu Li (UNH) Apr 20 4:00 pm Chemical Approaches to Artificial Photosynthesis Merck-Karl Pfister Lectures in Organic T.Y. Shen Lectures UNH, Room N104 (L103) Chemistry Prof. Christopher Dobson (Cambridge Univ.) 11:10 am Prof. Craig J. Hawker (U. California, Santa New Approaches to Understanding and Barbara) Preventing Neurodegenerative Disorders O’Malley Lecturer MIT, 6-120 MIT, 26-100 Prof. Hongjie Dai (Stanford University) 4:00 pm 4:00 pm Carbon Nanotubes for Biological Detection, Imaging and Therapy Prof. Charles M. Lieber (Harvard University) Apr 03 Boston College, Merkert 130 Nanoelectronics Meets Biology T.Y. Shen Lectures 4:00 PM Boston College, Merkert 127 4:00 pm Prof. Christopher Dobson (Cambridge Univ.) Apr 13 Defining the Mechanisms of Protein Folding and Apr 24 Unfolding O’Malley Lecturer Prof. Derek Pratt (Queen’s University, Canada) MIT, 26-100 Prof. Hongjie Dai (Stanford University) The Chemistry of Radical-Trapping 4:00 pm Graphene: from Nanoribbons to Hybrid Materials for Energy Storage and Conversion Antioxidants: Are Phenols Really Best? Boston College, Merkert 130 Boston College, Merkert 130 4:00 PM 4:00 PM Continued on page 13