Professor of Chemistry ,Director of the Institute of Organic Chemistry and Fine Chemicals
Academic Areas: Organic synthesis
Asymmetric catalysis is one of the most efficient ways to prepare optically pure organic compounds. Chiral amino alcohols represent an important type of highly versatile chiral building blocks for organic synthesis, especially for access to bioactive natural products and pharmaceutical agents. Hitherto, BOX-type and salen-type as two privileged classes of C2-symmetric ligands have been widely used in a great number of asymmetric metal-catalyzed reactions. Since the structure and electronic property of C1-symmetric ligands are more feasible to adjust, Our group focuses on design and synthesis of chiral N-ligands from natural amino acids and camphor, and their catalyzed asymmetric aldol reactions, nitroaldol reactions and Michael additions with aldehydes or enals to prepare chiral drug intermediates, involving fluorine-containing conpounds.
On the other hand, the smallest strained cyclopropenes are of particular interest for their unique structure and electronic properties. These three-membered carbocycles are extremely important versatile building blocks in organic chemistry. Recently, our lab developed one efficient method to get new type of reactive 2-acyl-cyclopropenecarboxylic esters. Now, we focuses on synthetic methodology for constructing bioactive carbocyclic and heterocyclic compounds starting from these novel reactive reagents.
1) Min Zhang, Fan Luo, and Yuefa Gong*. Stereoselective Cascade Formal Nucleophilic Substitution and Mannich Reaction of Ethyl 2‑Aroyl-1-chlorocyclopropanecarboxylates. J. Org. Chem. 2014, 79, 1335−1343.
2) Yirong Zhou, Yuequan Zhu, Shaobai Yan, and Yuefa Gong*. Copper-Catalyzed Enantioselective Henry Reaction of Enals and Subsequent Iodocyclization: Stereoselective Construction of Chiral
Azatricyclic Frameworks. Angew. Chem. Int. Ed. 2013, 52, 10265 –10269
3) Li, Yajun; Zhu, Jiangtao; Zhang, Lisi; Wu, Yongming*; Gong, Yuefa*. Synthesis of Fluorine-Containing Multisubstituted Phenanthridines by Rhodium-Catalyzed Alkyne [2+2+2] Cycloaddition and Tandem sp2 C-H Difluoromethylenation. Chemistry - A European Journal 2013, 19(25), 8294-8299.
4) Zhou, Yirong; Liu, Qiang; Gong, Yuefa*. Camphor-derived C1-symmetric chiral diamine organocatalysts for asymmetric Michael addition of nitroalkanes to enones. Org. & Biomol. Chem. 2012, 10(37), 7618-7627.
5) Lu, Deng-Fu; Zhou, Yi-Rong; Li, Ya-Jun; Yan, Shao-Bai; Gong, Yue-Fa*. Copper(II)-Catalyzed Asymmetric Henry Reaction of o-Alkynylbenzaldehydes Followed by Gold(I)-Mediated Cycloisomerization: An Enantioselective Route to Chiral 1H-Isochromenes and 1,3-Dihydroisobenzofurans. J. Org. Chem. 2011, 76 (21), 8869-8878.
6) Zhang, Jing-Li; Gong, Yue-Fa*. Cross-coupling reactions of two different activated alkenes through tetrabutylammonium fluoride (TBAF) promoted deprotonation/activation strategy: a regioselective construction of quaternary carbon centers. Org. Lett. 2011, 13(2), 176-179.
7) Zhou, Yirong; Dong, Junfang; Zhang, Fanglin; Gong, Yuefa*. Synthesis of C1-Symmetric Chiral Secondary Diamines and Their Applications in the Asymmetric Copper(II)-Catalyzed Henry (Nitroaldol) Reactions. J. Org. Chem. 2011, 76(2), 588-600.
8) Lu, Dengfu; Li, Yajun; Gong, Yuefa*. Organocatalytic Asymmetric Tandem Michael Addition-Hemiacetalization: A Route to Chiral Dihydrocoumarins, Chromanes, and 4H-Chromenes. J. Org. Chem. 2010, 75(20), 6900-6907.
9) Prolylprolinol-Catalyzed Asymmetric Michael Addition of Aliphatic Aldehydes to Nitroalkenes. Lu, Dengfu; Gong, Yuefa*; Wang, Weizhou, Adv. Synth. & Catal. 2010, 352(4), 644-650.
10) Zhang, Fang-Lin; Xu, Ai-Wen; Gong, Yue-Fa*; Wei, Mo-Hui; Yang, Xiang-Liang. Asymmetric Organocatalytic Four-Component Quadruple Domino Reaction Initiated by Oxa-Michael Addition of Alcohols to Acrolein. Chemistry--A European Journal 2009, 15(28), 6815-6818.
11) Luo, Fan; Lu, Dengfu; Gong, Yuefa*. Enantioselective bioreduction of 2-fluoro-2-alken-1-ols mediated by Saccharomyces cerevisiae. J. Mole. Catal. B: Enzymatic 2011, 70(3-4), 101-107.
Chinese Chemical Society (CCS)