Viresh H. Rawal Professor

Born India, 1958.
University of Connecticut, B.S., 1980.
University of Pennsylvania, Ph.D., 1986.
Columbia University, Postdoctoral Fellow, 1986-1988.
The Ohio State University, Assistant Professor, 1988-1994; Associate Professor, 1994-1995.
The University of Chicago, Professor, 1995-.

Accolades

Japan Society for the Promotions of Science (JSPS) Fellowship, 2015
Novartis International Chemistry Lectureship, 2007
Fellow of the American Association for the Advancement of Science, 2004
American Chemical Society Arthur C. Cope Scholar Award, 2003
Pfizer Research Award for Synthetic Organic Chemistry, 1995-1998
Merck Young Investigator Award, 1995
American Cyanamid Faculty Award, 1994
Eli Lilly Grantee Award, 1993-1995
American Cancer Society Junior Faculty Research Award, 1990-1993
DuPont Young Faculty Award, 1988-1989

OFFICE: SCL 334, 5735 S Ellis Ave, Chicago, IL 60637

PHONE: (773)702-2194

FAX: (773)702-0805

E-MAIL: vrawal@uchicago.edu

WEB: http://rawalgroup.uchicago.edu/

RESEARCH INTERESTS:

Chemistry is, ultimately, about chemical reactions-developing them, understanding them, and using them to make interesting, useful molecules. Much of the activity in my research group is aimed at discovering new ways to make complex molecules, including the design of unique strategies to certain families of natural products and the development of broadly effective methods for chemical synthesis.


The targets for our synthesis studies are selected for their intricate structures as well as their potent biological activities. We strive to devise routes that are concise, stereocontrolled, and high-yielding, and proceed through strategies that examine interesting aspects of structure and reactivity. Among the targets that we have successfully synthesized are: 5-oxo-silphiperfol-6-ene, (+)-tabersonine, geissoschizal, elisapterosin B, and strychnine.

 


The targets that we are currently pursuing include the clinically important anticancer agent vinblastine, and the potent antiviral and anticancer agent mycalamide A.

 


In recent years, a significant part of my group has focused on the development of effective catalysts for enantioselective reactions. The biologically important Aspidosperma family of alkaloids have provided the motivation for much of this work. We have found that salen-based chiral complexes catalyze the Diels-Alder reactions of amino-substituted dienes and a broad range of dienophiles, so as to produce the cycloadducts in high yields and excellent enantioselectivities.

 


Significantly, we have discovered that TADDOL, a simple, commercially available chiral alcohol, functions as a catalyst for highly enantioselective cycloadditions. Reminiscent of enzymes and antibodies, hydrogen bonding to TADDOL provides both tremendous rate acceleration and exquisite selection for the formation of one enantiomer of the product.


Selected References

1. Hydrogen Bonding by a Chiral Alcohol to an Aldehyde Catalyzes Highly Enantioselective Reactions. Huang, Y.; Unni, A. K.; Thadani, A. N.; Rawal, V. H. Nature, 2003, 424, 146. DOI: 10.1038/424146a.

2. Thadani, A. N.; Stankovic, A. R.; Rawal, V. H. Enantioselective Diels-Alder Reactions Catalyzed by Hydrogen Bonding. Proc. Natl. Acad. Sci. 2004, 101, 5846-5850. DOI:10.1073/pnas.0308545101.

3. Hayashida, J.; Rawal, V. H. "Total Synthesis of (+/-)-Platencin. Angew. Chem., Int. Ed. 2008, 47, 4373-4376. DOI: 10.1002/anie.200800756.

4. Malerich, J. P.; Hagihara, K.; Rawal, V. H. Chiral Squaramide Derivatives are Excellent Hydrogen Bond Donor Catalysts. J. Am. Chem. Soc. 2008, 130, 14416-14417. DOI: 10.1021/ja805693p.

5. Jewett, J. C.; Rawal, V. H. Temporary Restraints to Overcome Steric Obstacles: An Efficient Strategy for the Synthesis of Mycalamide B. Angew. Chem., Int. Ed. 2010, 49, 8682-8685. DOI: 10.1002/anie.201003361.

6. Bhat, V.; Allan, K. M.; Rawal, V. H. Total Synthesis of N-Methylwelwitindolinone D Isonitrile. J. Am. Chem. Soc. 2011, 133, 5798–5801. DOI: 10.1021/ja201834u.

7. Allan, K. M.; Kobayashi, K.; Rawal, V. H. A Unified Route to the Welwitindolinone Alkaloids: Total Syntheses of (−)-N-Methylwelwitindolinone C Isothiocyanate, (−)-N-Methylwelwitindolinone C Isonitrile, and (−)-3-Hydroxy-N-methylwelwitindolinone C Isothiocyanate. J. Am. Chem. Soc. 2012, 134, 1392–1395. DOI:10.1021/ja210793x.

8. Türkmen, Yunus E.; Montavon, Timothy J.; Kozmin, Sergey A.; Silver-Catalyzed Formal Inverse Electron-Demand Diels-Alder Reaction of 1,2-Diazines and Siloxy Alkynes. J. Am. Chem. Soc. 2012, 134, 9062-9065. DOI: 10.1021/ja302537j

9. Hutson, J. E.; Türkmen, Y. E.; Rawal, V. H. Salen Promoted Enantioselective Nazarov Cyclizations of Activated and Unactivated Dienones, J. Am. Chem. Soc. 2013, 135, 4988−4991. DOI: 10.1021/ja401908m.

10. Synthesis of alpha-Amino Acid Derivatives and Peptides via Enantioselective Addition of Masked Acyl Cyanides to Imines. Yang, K. S.; Rawal, V. H. J. Am. Chem. Soc. 2014, 136, 16148-16151. DOI: 10.1021/ja510135t.