The University of Iowa

Hien M. Nguyen

Hien M. Nguyen
Associate Professor
Phone: 
319-384-1887
Office: 
E433 CB
Biosketch: 
  • B.S., Tufts University (1996)
  • Ph.D., University of Illinois at Urbana-Champaign (2003)
  • NIH Postdoctoral Fellow, Stanford University (2004-2006)
Keywords: 

Organic and organometallic chemistry, new synthetic methodology, complex carbohydrates, natural product synthesis, transition metals-catalyzed stereoselective formation of glycosidic linkages, and carbon-carbon, carbon-nitrogen, as well as carbon-oxygen bonds, asymmetric catalysis, aminoglycoside antibiotics, tumor-associated mucin antigens, and cancer vaccine therapy.

Research Interests: 

Research in our group focuses on developing new methods and reagents that can potentially solve longstanding synthetic problems. In particular, we are interested in exploring transition metals-catalyzed stereoselective formation of C-C, C-O, and C-N bonds. The methods that we have developed will be applied as the key steps toward the synthesis of complex oligosaccharides, amphidinoline N, communesin B, and phorbaside C.

New Glycosylation Methods The development of new methods for stereoselective glycosylation has been extensively investigated due to the varied and important functions of carbohydrates in a variety of biological systems. Our group has developed several palladium and nickel catalysts that can effect glycosidic bond formation with excellent anomeric selectivity. Our methods rely on the nature of the catalysts rather than that of the protecting groups on the substrates to control the selectivity, thus eliminating the need for cumbersome protecting group manipulations.

Natural Product Synthesis We are also involved in the total synthesis of architecturally complex natural products. In each molecule, our goal is to develop new metal-catalyzed reactions that allow us to efficiently construct the key steps within the following biologically active natural products. In the metal-catalyzed asymmetric reactions, the asymmetric induction is generally controlled by the enationmerically pure ligands that are directly ligated to the metal atom. We are interested in utilizing carbohydrate-metal complexes as the chiral catalysts that are capable of promoting a variety of organic transformations.

 

Recent Publications: 
  • Arnold, J. S.; Nguyen, H. M. “Rhodium-Catalyzed Dynamic Kinetic Asymmetric Transformation of Racemic Tertiary Allylic Trichloroacetimidates with Unactivated Anilines.” J. Am. Chem. Soc. 2012 (revision).
  • Topczewski, J. J.; Tewson, T. J. Nguyen, H. M. “Iridium-Catalyzed Allylic Fluorination of Trichloro-acetimidates” J. Am. Chem. Soc.  2011, 133, 19318-19321.
  • Arnold, J. S.; Cizio, G. J.; Nguyen, H. M. “Synthesis of 1,1-Disubstituted Amines by Rhodium-Catalyzed Amination of Tertiary Allylic Trichloroacetimidates” Org. Lett. 2011, 13, 5576-5578.
  • Mensah, E. A.; Yu, F.; Nguyen, H. M.“Nickel-Catalyzed Stereoselective Glycosylation with C(2)-N-Substituted Benzylidene D-Glucosamine and D-Galactosamine Trichloroacetimidates for the Formation of 1,2-cis-2-Amino Glycosides. Applications to the Synthesis of Heparin Disaccharides, GPI Anchor Pseudodisaccharides, and a-GalNAc.” J. Am. Chem. Soc. 2010, 132, 14288-14302.
  • Arnold, J. A.; Stone, R. F.; Nguyen, H. M. “Rhodium-Catalyzed Regioselective Amination of Secondary Allylic Trichloroacetimidates with Unactivated Aromatic Amines.” Org. Lett. 2010, 12, 4580-4583.
  • Mensah, E. A.; Nguyen, H. M. “Nickel-Catalyzed Stereoselective Formation of a-2-Deoxy-2-Amino-Glycosides.” J. Am. Chem. Soc. 2009, 131, 8778-8780.
  • McKay, M. J.; Naab, B. D.; Mercer, G. J.; Nguyen, H. M. “Selective Formation of b-O-Aryl Glycosides in the Absence of the C(2)-Ester Neighboring Group.” J. Org. Chem. 2009, 74, 4705-4711.
  • Park, N. H.; Nguyen, H. M. “Stereoselective Rearrangement of Trichloroacetimidates: Application to the Synthesis of a-Glycosyl Ureas.” Org. Lett. 2009, 11, 2433-2436.
  • Mensah, E. A.; Azzarelli, J. A.; Nguyen, H. M. “Palladium-Controlled b-Selective Glycosylation in the Absence of the C(2)-Ester Participatory Group.” J. Org. Chem. 2009, 74, 1650-1657.
  • Mercer, G. J.; Yang, J.; McKay, M. J.; Nguyen, H. M. “Palladium-Catalyzed Rearrangement of Glycal Trichloroacetimidates: Application to the Stereoselective Synthesis of Glycosyl Ureas.” J. Am. Chem. Soc. 2008, 130, 11210-11218.
  • Yang, J.; Cooper-Vanosdell, C.; Mensah, E. A.; Nguyen, H. M. “Palladium-Catalyzed Stereoselective Glycosylation with Glycosyl Trichloroacetimidates” J. Org. Chem., Featured Article, 2008, 73, 794-800.