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Faculty
     
  Dr. John C.-G. Zhao
Professor

Office Phone: (210) 458-5432
Office: BSE 1.104A
E-Mail: cong.zhao@utsa.edu

Areas of Specialization
• Asymmetric synthesis and reactions
• Oxidation
• Phosphorus chemistry
• Small ring compounds





Research Interests

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.

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

Scheme 2. Base-Catalyzed Asymmetric Aldol Reactions



Recent Publications (since 2010)

 

1. Perera, S.; Sinha, D.; Rana, N. K.; Van, T.-D.; Zhao, J. C.-G.* “Highly Efficient Mannich Reaction Catalyzed by Modularly Designed Organocatalysts” J. Org. Chem. submitted.

 

2. Abbaraju, S.; Zhao, J. C.-G.* “Asymmetric Aldol Reaction of 3-Acetyl-2H-chromen-2-ones and Isatins Catalyzed by a Bifunctional Quinidine Urea Catalyst” Adv. Syn. Catal. under revision.

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3. Regati, S.; He, Y.; Thimmaiah, M.; Li, P.; Xiang, S.; Chen, B.;* Zhao, J. C.-G.* “Enantioselective Ring-Opening of meso-Epoxide by Aromatic Amines Catalyzed by a Homochiral Metal-Organic Framework” Chem. Commun., in press.

 

4. Guang, J.; Zhao, J. C.-G.* “Organocatalyzed asymmetric Michael reaction of β-aryl-α-ketophosphonates and nitroalkenes” Tetrahedron Lett., in press. DOI: 10.1016/j.tetlet.2013.08.015

 

5. Dai, Q.; Rana, N. K.; Zhao, J. C.-G.* “Highly Stereoselective Synthesis of 2,6-cis-Substituted Tetrahydropyrans Using a One-Pot Sequential Catalysis”, Org. Lett., 2013, 15, 2922-2925. DOI: 10.1021/ol400900h

 

6. Muramulla, S.; Ma, J.-A.; Zhao, J. C.-G.* “Michael Addition of Ketones and Aldehydes to Maleimides Catalyzed Modularly Designed Organocatalysts” Adv. Syn. Catal., 2013, 355, 1260-1264. DOI: 10.1002/adsc.201300041

 

7. Dai, Q.; Huang, H.; Zhao, J. C.-G.* “Highly Stereoselective Synthesis of Trisubstituted Cyclohexanols Using a Guanidine-Catalyzed Tandem Henry-Michael Reaction” J. Org. Chem., 2013, 78, 4153-4157. DOI: 10.1021/jo4001806

 

8. Sinha, D.; Perera, S.; Zhao, J. C.-G.* “High Enantioselective Inverse-Electron-Demand Hetero-Diels-Alder Reactions Catalyzed by Modularly Designed Organocatalysts” Chem. Eur. J. 2013, 19, 6976-6979. Highlighted by Synfacts(2013, page 0787). DOI: 10.1002/chem.201300168

 

9. Guo, Q.; Zhao, J. C.-G.* “Highly Enantioselective Three-Component Direct Mannich Reactions of Unfunctionalized Ketones Catalyzed by Bifunctional Organocatalysts” Org. Lett., 2013, 15, 508-511. DOI: 10.1021/ol303315c

 

10. Dai, Q.; Arman, H.; Zhao, J. C.-G.* “One-Pot Sequential Organocatalysis: Highly Stereoselective Synthesis of Trisubstituted Cyclohexanols” Chem. Eur. J. 2013, 19, 1666-1671. DOI: 10.1002/chem.201203104

 

11. Li, F.; Sun, L.; Teng, Y.; Yu, P.; Zhao, J. C.-G;  Ma, J.-A.* “Highly Diastereo- and Enantioselective Organocatalytic One-Pot Sequential 1,4-Addition/Dearomative-Fluorination Transformation” Chem. Eur. J. 2012, 18, 14255-14260. DOI: 10.1002/chem.201202636

 

12. Sinha, D.; Mandal, T.; Gogoi, S.; Goldman, J. J.; Zhao, J. C.-G.* “Asymmetric Aldol Reaction Catalyzed by Modularly Designed Organocatalysts” Chin. J. Chem., 2012, 30, 2624-2630. (Invited article) DOI: 10.1002/cjoc.201200639

 

13. 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, 53, 4870-4872. DOI: 10.1016/j.tetlet.2012.06.139

 

14. 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, 53, 4866-4869. DOI: 10.1016/j.tetlet.2012.06.140

 

15. 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

 

16. 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

17. 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

 

18. 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

19. 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.

 

20. 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

 

21. 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

 

22. 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

 

23. 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

 

24. 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

 

25. 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

 

26. 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

 

27. 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

 

28. 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

 

29. 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

 

30. 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

 

31. 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

 

32. 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

 

 

 

 

Zhao Group in June 2012

 

 

 

 

 

 

 


 

 





 

 

 

 

 

 

 

 

 

 

 

 

 

From front left: Swapna Konda (Ph D candidate); Savitha Muramulla (Ph D candidate); Santhi Abbaraju (Ph D candidate); Naresh Ramireddy (Ph D candidate)

Sandun Perera (Ph D candidate); Dr. Qunsheng Guo; Dr. Debarshi Sinha; Frances Morales;  

Dr. Qipu Dai; Dr. Muralidhara Thimmaiah; Dr. Nirmal Rana; John Zhao

Missing: Jie Guang (Ph D candidate)

 

 

 

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