研究领域

Asymmetrisynthesianreaction ;Oxidatio ;Phosphoruchemistr ;Smalrincompound

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.

近期论文

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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. 2014, 356: 237–241. Perera, S.; Sinha, D.; Rana, N.K.; Van, T.-D.; Zhao, J.C.-G. ""List–Barbas–Mannich Reaction Catalyzed by Modularly Designed Organocatalysts"" J. Org. Chem. 2013, 78 (21), 10947–10953. 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. 2013, 49, 9836-9838. Guang, J.; Zhao, J.C.-G. ""Organocatalyzed asymmetric Michael reaction of β-aryl-α-ketophosphonates and nitroalkenes"" Tetrahedron Lett. 2013, 54 (42), 5703–5706. 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. 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. 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. 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. 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. 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. 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. 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) 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. 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. 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. 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. Guo, Q.; Zhao, J.C.-G. ""Primary Amine Catalyzed Aldol Reaction of Isatins and Acetaldehyde"" Tetrahedron Lett. 2012, 53, 1768-1771. Bhanushali, M.; Zhao, C.-G. ""Organocatalyzed Enantioselective Aldol Reaction of 1H-Pyrrole-2,3-diones"" Tetrahedron Lett., 2012, 53, 359-362. Rout, L.; Regati, S.; Zhao, C.-G. ""Synthesis of α-Arylphosphonates using Copper-Catalyzed α-Arylation and Deacylative α-Arylation of β-Ketophosphonates"" Adv. Synth. Catal. 2011, 353, 3340-3346. 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. 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. 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. 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. Perera, S.; Naganaboina, V.K.; Wang, L.; Zhang, B.; Guo. Q.; Rout. L.; Zhao, C.-G. ""Organocatalytic Highly Enantioselective Synthesis of β-Formyl-α-hydroxyphosphonates"" Adv. Synth. Catal. 2011, 353, 1729-1734. 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. Bhanushali, M.; Zhao, C.-G. ""Developing Novel Organocatalyzed Aldol Reactions for the Enantioselective Synthesis of Biologically Active Molecules"" Synthesis 2011, 1815-1830. 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 Acetylene and Ethylene"" Nature Commun. 2011, 2, 204. 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. Samanta, S.; Perera, S.; Zhao, C.-G. ""Organocatalytic Enantioselective Synthesis of Both Diastereomers of α-Hydroxyphosphinates"" J. Org. Chem. 2010, 75, 1101-1106. 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.) 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. 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.