Our main research focus is developing high stereoselective methods for the synthesis of molecules with significant biological activities. We are also keen at studying the biological activities of our synthesized molecules through our existing collaborations within UTSA and with UTHSCSA. Our main goal is to conduct organic reactions in a green manner while achieving simultaneously high selectivities (chemo-, regio-, diastereo- and enantioselectivity). Our current research areas include: Asymmetric reaction and catalysis, organophosphorus compounds, and medicinal chemistry. For example, one of our current research areas is to use 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. We are also interested in developing base-catalyzed enantioselective aldol and Mannich reactions via the enolate mechanism (Scheme 2) and applying MOFs as catalysts in organic reactions. Through a successful collaboration with the UTHSCSA, we have identified several new compounds possessing anti-cancer activities out of the phosphonate and isatin derivatives.
1. Thimmaiah, M.; Li, P.; Regati, S.; Chen, B.;* Zhao, J. C.-G.* “Multi-component synthesis of 2-amino-6-(alkyllthio)pyridine-3,5-dicarbonitriles using Zn(II) and Cd(II) metal-organic frameworks (MOFs) under solvent-free conditions” Tetrahedron Lett., 2012, in press.
2. Guo, Q.; Zhao, J. C.-G.;* Arman, H. “Base-Catalyzed Three-Component Direct Mannich Reaction of Unmodified Ketones with High syn-Selectivities” Tetrahedron Lett., 2012, in press.
3. Guang, J.; Guo, Q.; Zhao, J. C.-G.* “Acetylphosphonate as a Surrogate of Acetate or Acetamide: Lewis Base-Catalyzed Enantioselective Aldol Reaction of Acetylphosphonates and Isatins” Org. Lett., 2012, 14, 3174–3177. DOI: 10.1021/ol301270w
4. Das, M. C.; Guo, Q.; He, Y.; Kim, J.; Zhao, C.-G.; Hong, K.; Xiang, S.; Zhang, Z.; Thomas, K. M.; Krishna, R.;* Chen, B.* “Interplay of Metalloligand and Organic Ligand to Tune Micropores within Isostructural Mixed-Metal Organic Frameworks (M’MOFs) for Their Highly Selective Separation of Chiral and Achiral Small Molecules” J. Am. Chem. Soc., 2012, 134, 8703-8710. DOI: 10.1021/ja302380x
5. Guo, Q.; Zhao, J. C.-G.* “Primary Amine Catalyzed Aldol Reaction of Isatins and Acetaldehyde” Tetrahedron Lett., 2012, 53, 1768-1771. DOI: 10.1016/j.tetlet.2012.01.108
6. Bhanushali, M.; Zhao, C.-G.* “Organocatalyzed Enantioselective Aldol Reaction of 1H-Pyrrole-2,3-diones” Tetrahedron Lett., 2012, 53, 359-362. DOI: 10.1016/j.tetlet.2011.11.056
7. Rout, L.; Regati, S.; Zhao, C.-G.* “Copper-Catalyzed a-Arylation and Deacylative a-Arylation of b-Ketophosphonates” Adv. Synth. Catal., 2011, 353, 3340-3346. DOI: 10.1002/adsc.201100605.
8. Ramireddy, N.; Abbaraju, S.; Zhao, C.-G.* “Organocatalyzed Enantioselective Synthesis of 2-Amino-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylates” Tetrahedron Lett., 2011, 52, 6792-6795. DOI: 10.1016/j.tetlet.2011.10.040
9. Li, P.; Regati, S.; Butcher, R. J.; Arman, H. D.; Chen, Z.; Xiang, S.; Chen, B.;* Zhao, C.-G.* “Hydrogen-Bonding 2D Metal-Organic Solids as Highly Robust and Efficient Heterogeneous Green Catalysts for Biginelli Reaction” Tetrahedron Lett., 2011, 52, 6220-6222. DOI: 10.1016/j.tetlet.2011.09.099
10. Abbaraju, S.; Bhanushali, M.; Zhao, C.-G.* “Quinidine Thiourea-catalyzed Enantioselective Synthesis of β-Nitrophosphonates: Beneficial Effect of Molecular Sieves” Tetrahedron, 2011, 67, 7479-7484. DOI: 10.1016/j.tet.2011.07.059
11. Guang, J.; Zhao, C.-G.* “Organocatalytic Enantioselective Tandem Aldol-Cyclization Reaction of α-Isothiocyanato Imides and Activated Carbonyl Compounds” Tetrahedron: Asymmetry, 2011, 22, 1205-1211. DOI: 10.1016/j.tetasy.2011.06.028
12. Perera, S.; Naganaboina, V. K.; Wang, L.; Zhang, B.; Guo. Q.; Rout. L.; Zhao, C.-G.* “Organocatalytic High Enantioselective Synthesis of b-Formyl-a-hydroxyphosphonates” Adv. Synth. Catal., 2011, 353, 1729-1734. DOI: 10.1002/adsc.201000835
13. Muramulla, S.; Zhao, C.-G.* “A New Catalytic Mode of the Modularly Designed Organocatalysts (MDOs): Enantioselective Synthesis of Dihydropyrano[2,3-c]pyrazoles” Tetrahedron Lett., 2011, 52, 3905-3908. DOI: 10.1016/j.tetlet.2011.05.092
14. Bhanushali, M.; Zhao, C.-G.* “Developing Novel Organocatalyzed Aldol Reactions for the Enantioselective Synthesis of Biologically Active Molecules” Synthesis, 2011, 1815-1830.DOI: 10.1055/s-0030-1260029
15. Xiang, S.; Zhang, Z.; Zhao, C.-G.; Hong, K.; Zhao, X.; Ding, D.; Xie, M.-H.; Wu, C.-D.; Gill, R.; Lobkovsky, E. B.; Thomas, K. M.; Chen, B. “Rationally
Tuned Micropores within Enantiopure Metal-Organic Frameworks for Highly Selective Separation of C2H2/C2H4” Nature Commun., 2011, 2, 204. DOI: 10.1038/ncomms1206
16. Guo, Q.; Bhanushali, M.; Zhao, C.-G.* “Quinidine Thiourea-Catalyzed Aldol Reaction of Unactivated Ketones: Highly Enantioselective Synthesis of 3-Alkyl-3-hydroxyindolin-2-ones” Angew. Chem. Int. Ed., 2010, 49, 9460-9464. Highlighted by Synfacts (2011, Page 103) DOI: 10.1002/anie.201004161
17. Samanta, S.; Perera, S.; Zhao, C.-G.* “Organocatalytic Enantioselective Synthesis of Both Diastereomers of a-Hydroxyphosphinates” J. Org. Chem. 2010, 75, 1101-1106. DOI: 10.1021/jo9022099
18. Ding, D.; Zhao, C.-G.* “Primary Amine-Catalyzed Biginelli Reaction for the Enantioselective Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones” Eur. J. Org. Chem., 2010, 3802-3805. Selected as one of the Most Accessed Articles of Euro. J. Org. Chem. DOI: 10.1002/ejoc.201000448
19. Ding, D.; Zhao, C.-G.*; Guo, Q.; Arman, H. “Enantioselective Synthesis of Bicylco[3.2.1]octan-8-ones Using an Organocatalyzed Tandem Michael-Henry Reaction” Tetrahedron, 2010, 66, 4423-4427. DOI: 10.1016/j.tet.2010.04.044
20. Ding, D.; Zhao, C.-G.* “Organocatalyzed Synthesis of 2-Amino-8-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitriles” Tetrahedron. Lett., 2010, 51, 1322-1325. DOI: 10.1016/j.tetlet.2009.12.139
Faculty
