B.S., Tufts University (1996) Ph.D., University of Illinois at Urbana-Champaign (2003) NIH Postdoctoral Fellow, Stanford University (2004-2006)

Organic Chemistry/Inorganic Chemistry

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.

Sletten, E.T.; Svec, R. L.; Nguyen, H.M. "Synthesis of a polymerizable, bivalent glycan mimetic of the HIV envelope spike gp120." Tetrahedron Lett. 2015, DOI: 10.1016/j.tetlet.2015.01.016 (Article in Press) Arnold, J. S; Zhang, Q.; Nguyen, H. M. "Transition-Metal-Catalyzed Allylic Substitutions of Trichloroacetimidates." Eur. J. Org. Chem. 2014, 4925-4948. McKay, M. J.; Park, N. H.; Nguyen, H. M. "Investigations of Scope and Mechanism of Nickel-Catalyzed Transformations of Glycosyl Trichloroacetimidates to Glycosyl Trichloroacetamides and Subsequent, Atom-Economical, One-Step Conversion to alpha-Urea-Glycosides." Chem. Eur. J. 2014, 20, 8691-8701 . Arnold, J. S.; Mwenda, E. T.; Nguyen, H. M. "Rhodium-Catalyzed Sequential Allylic Amination and Olefin Hydroacylation Reactions: Enantioselective Synthesis of Seven-Membered Nitrogen Heterocycles." Angew. Chem. Int. Ed. 2014, 53, 3688-3692. This article was selected as a "HOT PAPER." Zhang, Q.; Nguyen, H. M. "Rhodium-Catalyzed Regioselective Ring Opening of Vinyl Epoxides with Triethylamine Trihydrofluoride -Formation of Allylic Fluorohydrins." Chem. Sci. 2014, 5, 291-296. McKay, M. J.; Nguyen, H. M. "Recent Development in the Synthesis of Glycosyl Ureas." Carbohydrate Research, 2014, 385, 18-44 McConnell, M. S.; Mensah, E. A.; Nguyen, H. M. "Nickel-Catalyzed Stereoselective alpha-Glycosylation of Inositols - Application to the Synthesis of GPI Anchor Pseudo-Oligosaccharides." Carbohydrate Research, 2013, 381, 146-152. Arnold, J. S.; Nguyen, H. M. "Rhodium-Catalyzed Asymmetric Amination of Allylic Trichloroacetimidates." Synthesis, 2013, 45, 2101-2108. McConnell, M.S.; Yu, F.; Nguyen, H. M. "Nickel-Catalyzed alpha-Glycosylation of C(1)-Hydroxyl Group of Inositol Acceptors: A Formal Synthesis of Mycothiol." Chem. Commun. 2013, 49, 4313-4315. Arnold, J. S.; Cizio, G.; Nguyen, H. M. "Rhodium-Catalyzed Regio- and Enantioselective Amination of Racemic Secondary Allylic Trichloroacetimidates with Acyclic N- Methyl Anilines." Chem. Commun. 2012 , 48, 11531-11533. Yu, F.; Nguyen, H. M. "Studies on the Selectivity Between Nickel-Catalyzed 1,2-Cis-2-Amino Glycosylation of Hydroxyl Groups of Thioglycosides with C(2)-Substituted Benzylidene N-Phenyl Triflouroacetimidates and Intermolecular Aglycon Transfer of the Sulfide Group. " J. Org. Chem. 2012 , 77, 7730-7343. McKay, M. J.; Nguyen, H. M. "Recent Advances in Transition Metal-Catalyzed Glycosylation. " ACS Catalysis 2012,2, 1563-1595. Arnold, J. S.; Nguyen, H. M. "Rhodium-Catalyzed Dynamic Kinetic Assymetric Transformations of Racemic Tertiary Allylic Trichloroacetimidates with Anilines. " J. Am. Chem. Soc. 2012, 134, 8380-8383. Topczewski, J. J.; Tewson, T. J.; Nguyen, H. M. "Iridium-Catalyzed Allylic Flourination of Trichloroacetimidates." J. Am. Chem. Soc. 2011, 133, 19318-19321. Arnold, J. A.; Cizio, G.T.; Nguyen, H. M. "Synthesis of a,a-Disubstituted Allylic Aryl Amines by Rhodium-Catalyzed Amination of Tertiary Allyic 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 Galactosamine Trichloroacetimidates for the Formation of 1,2-cis-2-Amino Glycosides. Applications to the Synthesis of Heparin Disaccharides, GPI Anchor Psuedodisaccharides, and alpha-GalNAc." J. Am. Chem. Soc. 2010, 132, 14288-14302. Arnold, J. S.; 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 Formatin of alpha-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 beta-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 Stereoselective Synthesis of Glycosyl Ureas." Org Letters. 2009, 11, 2433-2436.