Research Interests

Our research focus is to conduct organic reactions in a green manner, aiming at achieving high selectivities (chemo-, regio-, diastereo- and enantioselectivity) during the reaction. Our current research areas include: Asymmetric reaction and catalysis; small-ring compounds; oxidation; and organophosphorus compounds. Instead of isolating these areas, we try to combine two or more of them together in our studies to gain better insights and/or results. Now we are vigorously pursuing the idea of using modularly designed self-assemblies as the organocatalysts for asymmetric reactions (Scheme 1). This new method for the formation of organocatalysts drastically reduces the efforts required for the synthesis and modification of an organocatalyst.

Scheme 1. Modularly Designed Organic Self-Assembly for Highly Enantioselective Direct Nitro-Michael Addition

Selected Publications

“Enantioselective Synthesis of α-(3-Hydroxypyrazol-1-yl) Ketones Using an Organocatalyzed Michael Addition Reaction”
Gogoi, S.; Zhao, C.-G.*, Ding, D.
Org. Lett., 2009, 11, in press.

“Modularly Designed Organocatalytic Assemblies for Direct Nitro-Michael Addition Reactions”
Mandal, T.; Zhao, C.-G.
Angew. Chem. Int. Ed. 2008, 47, 77-14-7717.
[Highlighted by Synfacts (2009, Page 95)]

“Inverse-Electron-Demand Hetero-Diels-Alder Reaction of α, α-Unsaturated -Ketophosphonates Catalyzed by Prolinal Dithioacetals”
Samanta, S.; Krause, J.; Mandal, T.; Zhao, C.-G.
Org. Lett., 2007, 9, 2745-2748.
(Highlighted by the Organic-Chemistry.org)

“Organocatalytic Highly Enantioselective Nitroaldol Reaction of α-Ketophosphonates and Nitromethane”
Mandal, T.; Samanta, S.; Zhao, C.-G.
Org. Lett. 2007, 9, 943-945.

“Silver(I) Triflate-Catalyzed Direct Synthesis of N-PMP Protected α-Aminopropargylphosphonates from Terminal Alkynes”
Dodda, R.; Zhao, C.-G.
Org. Lett., 2007, 9, 165-167.
(Highlighted by Organic-Chemistry.org)

“Organocatalytic Highly Enantioselective Synthesis of Secondary α-Hydroxyphosphonates”
Dodda, R.; Zhao, C.-G.
Org. Lett., 2006, 8, 4911-4914.
[Highlighted by Synfacts (2006, Page 1282)]

“Catalytic Highly Enantioselective CH Oxidation of vic-Diols with Shi’s Oxazolidinone Dioxiranes”
Jakka, K.; Zhao, C.-G.
Org. Lett., 2006, 8, 3013-3015.

“Organocatalytic Enantioselective Synthesis of α-Hydroxy Phosphonates”
Samanta, S.; Zhao, C.-G.
J. Am. Chem. Soc., 2006, 128, 7442-7443.

''C₂-Symmetric Bisprolinamide as Highly Efficient Catalyst for Direct Aldol Reaction''
Samanta, S., Liu, J.; Dodda, R.; Zhao, C.-G.
Org. Lett., 2005, 7, 5221-5123.
(Highlighted by the Organic-Chemistry.org)

''Some New Aspects of the Boyer Reaction'
Chakraborty, R.; Franz, V.; Bez, G.; Dipali, V.; Popuri, C.; Zhao, C.-G
Org. Lett., 2005, 7, 4145-4148.

Current Grants

1. National Institutes of Health-National Institute of General Medical Sciences (1SC1GM082718-01A1), “Enantioselective Synthesis of Phosphinate Derivatives”, direct cost $725,000 ($1,035,165 total cost); 2009-2012, Role: PI.

2. The Welch Foundation, “Enantioselective Synthesis of α-Hydroxy-β-nitrophosphonic Acid Derivatives” (AX-1593), direct cost $150,000; 2007-2010, Role: PI

Research Group Members

• Dr. Vijaya Kumar Naganaboina (post-doctoral researcher)
• Dr. Derong Ding (Post-doctoral researcher)
• Sandun Perera (Ph D candidate)
• Savitha Muramulla (Ph D candidate)
• Naresh Ramireddy (Ph D candidate)
• Nicholle Reinhardt (MS candidate)
• Wen Kuo (MS candidate)
• Joshua Goldman (undergraduate)

Job Openings

Open positions for graduate students and postdoctoral research associates are available at Dr. Zhao's group. With solid training on Organic Chemistry and Materials Science, those who are enthusiastic, ambitious and determined to develop excellent academic and industrial careers are particularly welcome.

Resources

Besides the research facility at the Chemistry Department, we have the following major research instrument in our lab: Shimadzu HPLC system, Shimadzu Prominence HPLC system, Agilent GC (HPLC and GC have chiral columns for separating enantiomers), Agilent UV, Ozone Generator

News



The most comprehensive monograph on dioxirane chemistry coauthored by Dr. Zhao has been recently published by Wiley: ISBN: 978-0-470-45407-7

Mr. Jie Guang recently received his visa and will join our group in this August as a Ph D candidate.