Written by: Nate Wallock, Ph.D

We are pleased to announce the 2009 winners of the annual Aldrich Chemistry Graduate Student Innovation Award (GSIA) program.  In this sponsorship, selected universities are invited to nominate their outstanding graduate students performing research in the area of synthetic organic chemistry methodology.  The GSIA award consists of a monetary award to support the student's research efforts and a travel allowance to attend a scientific meeting.  Additionally, award program culminates with a symposium at our Sigma-Aldrich site in Milwaukee where the students have the opportunity to present their research, tour our facilities, and visit with key personel in the Aldrich Chemistry group.

This year, the following four students have been selected to receive awards:

Brett Fors, MIT (Prof. Stephen Buchwald)
Andrew Young, U. of Illinois (Prof. M. Christina White)
Nathan Werner, U of Illinois (Prof. Scott Denmark)
Eric Gillis, U of Illinois (Prof. Martin Burke)

Written by Louis-Charles Campeau Ph. D.
Senior Research Chemist
Process Research & Development
Merck FrosstCentre for Therapeutic Research

 The prevalence of indoles in natural and medicinal bioactive compounds has stimulated much interest in the development of synthetic methods for their preparation.  Recently, Fagnou and co-workers have discovered that oxidative coupling of acetanilides with di-substituted alkynes using Rhodium catalysis provides good  yields of the corresponding indole products.  This novel reactivity allows for a broader range of readily available starting materials to be used, as simple anilines can be easily acetylated to provide the aryl building block.  The authors demonstrated this by coupling a number of substituted acetanilides and alkynes.  Good regioselectivity was demonstrated when more than one indole isomer could be formed. 

 

I came across this incredibly useful and straight-forward asymmetric preparation of allylic amines in the ASAP articles of the Journal of the American Society. The efficient asymmetric preparation of allylic amines has been a longstanding challenge in organic chemistry. While the Rh(I)-catalyzed addition of arylboron reagents to activated imines has been demonstrated, the analogous addition of alkenylboron species to activated imines to provide allylic amines remained unprecedented until now. Brak and Ellman have now shown the addition of alkenyl trifluoroborates to both aromatic and aliphatic activated N-tert-butylsulfinyl imines using a catalyst comprised of [Rh(OH)(cod)]₂, and dpp-benzene, in the presence of NEt₃ and H₂O/DMF. The scope is quite broad, with respect to both coupling partners, incorporating variously substituted amines and both di-and tri-substituted olefinic trifluoroborates, in all cases providing the allylic amines with excellent diastereoselectivity. What is also worth mentioning is the analogous transformation with a boronic acid instead of the trifluoroborate salt provided the product, albeit in low yield; thus, key to this chemistry is the use of the stable boronic acid surrogate trifluoroborate salts. This method is likely to be quite useful to the chemist for the facile and stereoselective prepararion of allylic amines.

Brak, K.; Ellman, J. J. Am. Chem. Soc. ASAP.

The 2009 Pittcon Heritage Award will be presented to Alfred R. Bader, Founder of Aldrich Chemical Company, owner of Alfred Bader Fine Arts. The award will be presented in the Opening Session, which begins at 4:30 p.m. on March 8 at the Pittcon Conference, taking place in Chicago from March 8-13, 2009.

This award recognizes outstanding individuals whose entrepreneurial careers shaped the instrumentation and laboratory supplies community, inspired achievement, promoted public understanding of the modern instrumentation sciences, and highlighted the role of analytical chemistry in world economies.
Alfred Bader established the Aldrich Chemical Company, later the Sigma-Aldrich Corporation, as one of the world’s leading suppliers of research chemicals. These research chemicals are essential tools for chemists of all kinds, used as key reagents and starting materials. During Bader’s long tenure at the firm, from 1951 to 1991, he oversaw the assembly of a huge library of rare chemicals—numbering nearly 50,000—in addition to thousands of more commonly used chemicals. The company’s annual catalog, which featured a red “A” on the binding and a reproduction of fine art on the cover, became widely known as “Big Red” and was often used as a reference for its physical data and structural information.

http://www.chemheritage.org/events/event-nav2-pittcon.html