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Hao Xu

Assoc. Prof./Synthetic Chem./Chem. Biology
Education

B.S. (2001): Peking University, Beijing, People’s Republic of China
Ph.D. (2006) : Scripps Research Institute, La Jolla, CA
Camille and Henry Dreyfus Postdoctoral Fellow (2006–2010) : Harvard University, Department of Chemistry and Chemical Biology, Cambridge, MA

Specializations

Synthetic Chemistry, Chemical Biology

Biography

Education Background:

Harvard University
Department of Chemistry and Chemical Biology, Cambridge, MA (2006–2010)
Camille and Henry Dreyfus Postdoctoral Fellow with Professor Eric N. Jacobsen

The Scripps Research Institute, La Jolla, CA (2001–2006)
Degree Awarded: Ph.D. in Synthetic Organic Chemistry
Thesis Advisor: Professor K. C. Nicolaou

Peking University, Beijing, People’s Republic of China (1997–2001)
Degree Awarded: B.S. in Chemistry

Awards and Honors:

NSF CAREER Award (2014)
Thieme Chemistry Journal Award (2014)
Harvard University Postdoctoral Travel Grants Award (2008)
Stereochemistry GRC for Exceptional Accomplishments in Organic Chemistry Chair’s Award (2008)
Camille and Henry Dreyfus Postdoctoral Fellowship (2007–2009)
Bristol–Myers Squibb Graduate Fellowship in Synthetic Organic Chemistry (2005–2006)
Lesly Starr Shelton Award for Excellence in Chemistry Graduate Studies (2005)
Skaggs Research Predoctoral Fellowship (2003–2006)
Wu–Si Award for Outstanding Junior Students in Peking University (1999–2000)
Peking University President Award for Outstanding Freshmen (1998–1999)
Finalist and Silver Medal in the National Chemistry Olympiad, China (1997)
Finalist and Bronze Medal in the National Physics Olympiad, China (1996)

Research Interests:
Welcome! We are a group of scientists who are interested in novel chemical reactivity and selectivity, especially in catalytic processes. We are engaged in two dynamic areas of chemical synthesis: complex-molecule synthesis and functional synthesis at the chemistry–biology interface.

Complex-molecule synthesis has had tremendous impact on the development of chemistry, biology and medicine. However, it is a misconception that chemical synthesis is a mature discipline. Lengthy synthetic sequences and low overall yields in most multi-step syntheses make it extremely challenging to provide sufficient quantities of desired targets for therapeutic purposes. The inefficiency is often due to the limited availability of chiral building blocks and our limited capability to control selectivity. The discovery of powerful selective catalytic reactions will significantly increase the efficiency of complex-molecule synthesis. The long-term goal of our research program is to design and discover selective catalytic reactions for efficient complex-molecule synthesis, and to supply sufficient quantities of targets for biological studies. Further mechanistic study and synthetic application of these reactions will allow for rapid syntheses of various complex targets.

Selective labeling of bio-macromolecules (proteins in particular) in living cells offers chemists and biologists new opportunities to investigate biological phenomena at the molecular, cellular or organismal level. Chemical labeling with small-molecule probes, a complementary approach to classic enzymatic labeling methods, has emerged as a unique tool for biologists. The long term goal of this research program is to design and discover robust ligation reactions under physiological conditions, and to apply them to selectively label various bio-macromolecules in vivo.

Publications

Representative Publications

  1. Liu, G. S.; Zhang, Y. Q.; Yuan, Y. A.; Xu, H.* “Iron(II)-Catalyzed Intramolecular Aminohydroxylation of Olefin with Functionalized Hydroxylamines.” J. Am. Chem. Soc. 2013, 135, 3343.
  2. Lu, D. F.; Zhu, C. L.; Xu, H.* “Copper(I)-Catalyzed Diastereoselective Hydroxytrifluoromethylation of Dienes Accelerated by Phosphine Ligands.” Chem. Sci. 2013, 4, 2478.
  3. Zhang, Y. Q.; Yuan, Y. A.; Liu, G. S.; Xu, H.* “Iron(II)-Catalyzed Asymmetric Intramolecular Aminohydroxylation of Indoles.” Org. Lett. 2013, 15, 10.1021/ol401666e
  4. Zhang, Y. Q.; Liu, J. D.; Xu, H.* “Copper(II)-Catalyzed Trifluoromethylation of N-Aryl Imines.” Org. Biomol. Chem. 2013, 11, 10.1039/C3OB41283K
  5. Liu, G. S.; Wilkerson, P. D.; Toth, C. A.; Xu, H.* “Highly Enantioselective Cyclizations of Conjugated Trienes with Low Catalyst Loadings: A Robust Chiral NHC Enabled by Acetic Acid Cocatalyst. Org. Lett. 2012, 14, 858.
  6. Xu, H.; Zuend, S. J.; Woll, M. G.; Tao, Y.; Jacobsen, E. N. “Asymmetric Cooperative Catalysis of Strong Brønsted Acid-Promoted Reactions using Chiral Ureas.” Science 2010, 327, 986.
  7. Xu, H.; Jacobsen, E. N. “Enantioselective Catalytic Povarov Reactions to Access Stereochemically Rich Tetrahydroquinolines. Asymmetric Catalysis of Strong Brønsted Acid-Promoted Reactions Using Chiral Ureas.” Nat. Protoc. 2014, in press.
  8. Gerard, B.; O’Shea, M. W.; Donckele, E.; Kesavan, S.; Akella, L. B.; Xu, H.; Jacobsen, E. N.; Marcaurelle, L. A. “Application of a Catalytic Asymmetric Povarov Reaction using Chiral Ureas to the Synthesis of a Tetrahydroquinoline Library.” ACS Comb. Sci. 2012, 14, 621.
  9. Nicolaou, K. C.; Xu, H.; Wartmann, M. “Biomimetic Total Synthesis of Gambogin and Rate Acceleration of Pericyclic Reactions in Aqueous Media.” Angew. Chem. Int. Ed. 2005, 44, 756.
  10. Nicolaou, K. C.; Sasmal, P. K.; Xu, H. “Biomimetically Inspired Total Synthesis and Structure Activity Relationships of 1-O-Methyllateriflorone. 6π Electrocyclizations in Organic Synthesis.” J. Am. Chem. Soc. 2004, 126, 5493.