My main interest lies in the chemistry of chiral iodine reagents. We are interesting in making chiral benziodanes as shown in the figure below, and using these reagents to perform asymmetric addition reactions to monosubstituted alkenes. I have a continuing research collaboration with Professor Thomas Wirth, Cardiff University, in Wales. My students have the opportunity to spend a summer working in Wales, when funding is available. Typically, students work in my lab during the summer after they complete organic chemistry, then continue through the following academic year, then work in the Wirth Laboratory during the summer following.
Funding for this research has come from a variety of sources over the years. The Research Corporation funded my research program from 1995 - 1999, providing additional funding to pay for the initial visit to Switzerland in 1999. Subsequent summers in Switzerland and more recently, Cardiff, Wales, have been funded by the National Science Foundation's International Opportunity for Scientists and Engineers (SBE Division, 2000 - 2002). In the summer of 2002 The NSF renewed my grant for an additional three years (2003 - 2006). In the fall of 2002, the American Chemical Society granted us a PRF-B grant for research going on at Albion College. The Royal Society, London, granted me a USA Fellowship for my sabbatical year in Wales in 2003-2004.
Local support has been more than generous, coming from Albion College's Blanchard Fellowship(1998), Academic Affairs Office, Faculty Development Committee, and with funding for Student stipends, FURSCA. For all of these grants I am truly grateful, for without consistent funding our research program would be impossible. It is equally clear that, without outstanding research efforts by my students, funding would not be forthcoming. For their effort I am also grateful. Below are the student research efforts for the past nine years.
| 1998 Highlights | 1999 Highlights |
| 2000 Highlights | 2001 Highlights |
| 2002 Highlights | 2003 Highlights |
| Sabbatical Highlights | 2005 Highlights |
| 2006 Highlights | 2007 Highlights |
The summer of 1998 saw two students working in my lab on this project. Each tried to synthesize chiral nonracemic 3-phenylbenziodoxole acetate.
Steve Reitz, '00 attempted to synthesize chiral non-racemic 2-iodobenzhydrol, an intermediate in the synthesis of the above compound, via an asymmetric reduction of 2-iodobenzophenone. Here are a couple of pictures of him doing a column.
Steve worked for Pharmacia in Kalamazoo, MI, as an organic chemist in Drug
Discovery for three years and is now finishing up Medical School at Toledo.
Rachel Hector, '00 chose to synthesize the same chiral compound as Steve using a chiral resolution of the racemic 2-iodobenzhydrol. Rachel is using Cross-Linked Enzyme Crystals (CLECs)
furnished by Altus Biologics to do the resolution via an asymmetric acylation. She has performed the screening and has selected three enzyme systems to optimize. Here are some pictures of her doing the screening.
Rachel completed her Ph.D. at Illinois - Champaign-Urbana inthe Spring of 2006
and is now doing a post-doc in Boston.
In the winter of 1999, we were invited to collaborate with Thomas Wirth at the Institute of Organic Chemistry at the University of Basel, Switzerland. Rachel, my family, and I traveled to Basel for a summer of research collaboration and fun with the Wirth Group. Our efforts have resulted in the synthesis of our first chiral reagent and its evaluation as an addition reagent to alkenes. Our work was published in the European Journal of Organic Chemistry (2001, page 1569). Below is a picture of us and the Wirth Group in Switzerland.
Rachel presented her results at the National ACS Meeting in Anaheim in 1999 and in San Francisico in 2000 in the CHED Division's Undergraduate Research Poster session. Pictures below.
Rachel Hector also wrote her Honors Thesis, graduated in the spring of 2000.
The Summer of 2000 saw two students, Danielle Willsie, '01, and Sarah Burpee, '01, travel to Switzerland to work with the Wirth Group. Here at Albion, two students; Jocelyn Jacobs, '02, and Amanda Boye, '02, worked in my lab on the synthesis of two new chiral hypervalent iodine reagents. Each received funding from Albion College's new Foundation for Undergraduate Research, Scholarship and Creative Activity (FURSCA). Sarah, Amanda, and Jocelyn presented their work at the National ACS Meeting in San Diego in 2000 in the CHED Division's Undergraduate Research Poster session.
Sarah and Danielle wrote Departmental Honors theses, and graduated in the Spring of 2001. Danielle got a job working for PTC Pharmaceutics in New Jersey as an organic chemist, completed an advanced degree in Athletic Training at Rutgers University, and is a professional athletic trainer. Sarah completed Medical school at the University of Des Moines, Iowa and is now a practicing physician in Grand Rapids, MI. Jocelyn is working toward her teaching certificate and is doing substitute teaching.
The Summer of 2001 saw Amanda Boye, '02, travel to the University of Cardiff, in Wales, to work with the Wirth Group (Thomas Wirth had accepted a position there in the fall of 2000). She worked on lactonization reactions with hypervalent iodine reagents. That's Amanda in the middle.
That same Summer, Josh Konzer, '02, went to Notre Dame University to work with a friend of Thomas' on some theoretical aspects of hypervalent iodine reagents. Here at Albion College, Crystal Ingison,'03, and Laurie Vance,'03, worked in my lab on two new synthetic targets; a chiral diamine ligand based on Wulff's VANOL Ligand system, and new methodology to access new chiral hypervalent iodine reagents. Below are some pictures of our Summer 2001 adventure. Amanda Boye is working toward her Ph.D. at Illinois- C-U, after working for a year in Germany. Josh went onto Physics Graduate school after working toward a Chemical Engineering degree at Washington University in St. Louis. Laurie Vance is finishing up Medical School at Wayne State University.
Each of these four presented their research work at the National ACS Meeting in Orlando in the Spring of 2002. Here is a picture!
The Summer of 2002 saw two students, Joe Heinzelmann and Craig Streu working on the synthesis of a new chiral hypervalent reagent. While they were unsuccessful at completing this synthesis due to the unavailability of a reagent (post 9-11) the summer was informative. Below are some pictures of the summer research effort.
The summer of 2002 also saw Crystal Ingison travel to Cardiff to work with my collaborator, Thomas Wirth, at Cardiff University. There she worked on lactonization reactions of alkenoic acids using hypervalent iodine reagents, continuing and completing the research started by Amanda Boye. The results of their combined research were accepted by Organic Letters (2003, 5(12), 2157-2159). Here are some pictures! Crystal completed her M.S. At Illinois and is now working at the Mayo Clinic in Minnesota.
These three presented their research results at the Spring Meeting of the ACS in New Orleans.
Starting in the summer of 2003 I was on sabbatical. I was a Royal Society USA Research Fellow at Cardiff University, working with Thomas Wirth. Craig Streu, '04, and Joe Heinzelmann, '04 were in Cardiff during that summer working on two projects with Thomas. I joined the Wirth Group in August. Craig is working toward his Ph. D. in Chemsitry at U.Penn and has recently published his work in Angewandte Chemie!! Joe is working as a professional Chemist.
My sabbatical, to the say the least was a fantastic experience. I worked on a number of projects, some were successful, other were not. The completion of a project that Crystal, Craig, and Amanda had worked was the first project, which, sad to say, failed in the final oxidation step. The rest of the fall was spent on a number of other projects, and the completion of a review paper that was published in Chemical Society Reviews (Chem. Soc. Rev., 2004, 33, 354 – 362.). The spring saw a new project, the use of hypervalent iodine reagents as tetrahydrofuranylating agents, using microwaves to facilitate the reaction. This short communication was published in Synlett (Synlett, 2004 (13) 2291 – 2293). In the Spring of 2004, we organized and held the Cardiff Symposium on Hypervalent Iodine Chemistry. Most of the Major researchers from around the world attended and a great time was had by all!!
In addition to all this hard work in the the lab, I did find time to travel with my family, while we lived in Wales. Trips to London, Bath, Bristol, Durham, Edinburgh, Switzerland, Germany, as well as all over Wales, highlighted our year in the UK. Below are pictures.
At the Royal Society Office with Isaac Newton, a prominent member of the Royal Society
On top of Camera Obscura in Edinburgh, note rainbow?
Edinburgh Castle from the Botanical Garden
Durham Cathedral and With Grad students in Carreg Cennon (in Wales)
London Eye and Big Ben
The London Museum of Natural History Main Hall
Bath Museum in . . . Bath!
St. David's Cathedral in our Illinois Colors.
The 2004-2005 Academic year saw my return to Albion and the arrival of 3 new students to my lab; Neil Forster, Shauna Paradine and Beth Gruber, the latter two as Student Research Partners (First-years). We also saw the beginning of new target compounds.
The summer 2005 gave us the opportunity to move into our new Building, Kresge Science Hall, nicknamed "the Bruce" after Bruce Kresge, our major donor for the building, and long-time supporter of Albion College. Three students; Shauna Paradine, Sarah Simmons and Bethany Bierlein spent the summer moving us into the new lab and working on three new targets. While we were unsuccessful in making any new hypervalent iodine reagents, we are hopeful for future success. Below are a few photos of our new labs and us working in them!!
Bethany was crowned Miss Calhoun County during the summer, so we crowned her with an appropriate crown ether at lunch!!
The fall of 2005 saw two new additions to the lab; Meg Schaefer and Thomas Freeman, both Student Research Partners. Shauna, Sarah and Bethany continued in the lab with Bethany and Shauna working with Meg, and showing her the ropes. Thomas, wishing a more biochemical slant to his research experience, began, but did not complete, a synthesis of a ribonucleotide using as a first step, the Dess-Martin Periodinane oxidation of a suitably protected Sugar. Thomas will be joining the Chris Rohlman Group, now that Dr. Rohlman is back from his sabbatical.
The Summer of 2006 was the final year of our current NSF grant and saw Sarah and Shauna travel to Wales to work with Thomas. Shauna continued her project begun at Albion, completing her synthesis and evaluation of her target compound. A publication is in draft form, we hope to have it submitted by the end of the year. Sarah, wishing to try new things, tried some new nitrogen-based hypervalent iodine chemistry. They enjoyed their time in Wales, but are glad to be back; for Sarah to begin working on her Senior Departmental Honors Thesis, for Shauna to continue to work on her project and begin thinking about her next International research adventure, hopefully to the University of Mainz, to work in the Lab of Prof. Dr. Bernhard Witulski, another hypervalent Iodine chemist, with applications to materials Science. Dr. French spent his summer as Director of FURSCA and trolling the funding waters for new funding opportunities.
The Summer of 2007 Saw Dr. French continue as summer FURSCA Director, though for only the first half of the summer. We welcomed two new members to the groups this summer; Teresa Giacomazzi, and William Andert, both who spent 5 weeks at Albion working on new Chiral hypervalent iodine reagents. Shauna Paradine, in her final summer as an Albion college student, was able to accept a RISE Fellowship through the American Chemical Society, and spend the summer at the University of Mainz, working in the Lab of Prof. Dr. Bernhard Witulski, another hypervalent Iodine chemist, with applications to materials Science. Her project was successful enough to warrant her fourth ACS National meeting presentation in Boston in August. Dr. French spent July in Mainz as well, at the invitation of Professor Witulski, and team taught a class on heterocyclic chemistry to upper class students at Mainz. While the NSF and DFG said "no" to out joint collaborative proposal, a strong collaboration was established and we are hopeful for funding from other sources to pay for Albion students to travel to either Mainz or Cardiff in the coming summers.
DR. ANDREW N. FRENCH
Chemistry Department
Albion College
Albion MI 49224
afrench@albion.edu