个人简介

Ph.D., University of Arizona (Victor Hruby), 1995; Postdoctoral, The Scripps Research Institute (Barry Sharpless), 1995-97 Associate Editor, Molecules Associate Editor, ISRN-Organic Chemistry Board Member, CHEMTRACTS-Organic Chemistry Board Member, Chemical Biology & Drug Design Editorial Advisory Board, Natural Products Against Cancer Honorary Editorial Board Member, Reports in Organic Chemistry

研究领域

Organic, Medicinal and Bioorganic Chemistry

Asymmetric Synthesis Asymmetric Catalysis Bioorganic and Medicinal Chemistry Professor Li is interested in the development of new concepts, new achiral and chiral reagents, new reactions, their asymmetric versions and applications. He is also interested in bioorganic and medicinal chemistry, especially, in the study of new analgesic and anti-inflammatory agents, peptide and peptidomimetic drug design, synthesis and structure-activity-relationship (SAR) studies that are important for treating diseases, such as AIDS, cancer and diabetes. So far, Professor Li and his coworkers/collaborators have achieved nearly 200 publications (H-index of 37). Recently, Li group has established a new concept called GAP chemistry (Group-Assistant-Purification chemistry), new phosphoramides and phosphinamides, N-phosphonyl and N-phosphinyl imine chemistry. His group has successfully utilized chiral N-phosphonyl and N-phosphinyl imines to many asymmetric reactions of chemically and biomedically importance. Professor Li's research has been supported by the National Institutes of Health (NIH), the Robert Welch Foundation, the South Plains Foundation, TTU REF grants and National Science Foundation (NSF as Co-PI). Some of the research conducted by the Li group at Texas Tech University is summarized below. The GAP chemistry concept The GAP chemistry means Group-Assistant-Purification chemistry. It is well-known that the development of efficient syntheses that combine economic, environmental and green aspects constitutes a great challenge in modern organic chemistry. It has been extremely difficult to find general achiral and chiral reagents that enable organic synthesis, particularly, asymmetric synthesis and catalysis, to be performed without the use of traditional purifications of chromatography or recrystallization. So far, such a chemistry concept with atom economic advantages has not been established. However, this new concept would encourage the synthetic community to search for efficient reagents and related reactions to better serve for academic and pharmaceutical industry with minimized use of energy, materials and manpower. As shown below that the Li group has discovered that a series of reactions involving chiral N-phosphonyl and N-phosphinyl imines can meet the requirements of GAP chemistry, i.e. the pure chiral amino isomeric products attached with chiral N-phosphonyl or N-phosphinyl group can be obtained simply by washing the solid crude products with hexane or the mixture solvent of hexane-EtOAc. Furthermore, the achiral or chiral N-phosphonyl auxiliary can be easily cleaved under mild conditions, and can be quantitatively recycled by a one-time extraction with n-butanol. Fig 1. GAP chemistry Pictorial Description GAP chemistry is the first concept which connects chemical reactions and reagents with separation and purification techniques. Advantages of GAP chemistry: (1) Decrease waste production (e. g., a 15 people-group may need 500 kg silica gels and 1000 L solvents annually); (2) Reduce synthesis expenses (silica gels, solvents, manpower, energy, apparatus, etc.); (3) Accelerate synthesis processes; (4) Avoid shortcomings of both solid-phase-peptide and liquid-phase-peptide synthesis (SPPS and LPPS). Requirements of GAP Chemistry: well-designed groups are crucial for GAP Chemistry. These groups should be able to: (1) generate adequate reactivity for their attached reagents; (2) control diastereoselectivity (for chiral GAP reagents); (3) control enantioselectivity (for achiral GAP reagents in asymmetric catalysis); (4) control solubility of resulting products (insoluble or nearly insoluble in some solvents such as hexane, petroleum ethers, their co-solvents with EtOAc, etc.; but soluable in common synthetic solvents such THF, DCM, etc.); (5) be recovered and recycled for re-use; (6) be adjusted readily to reach the aims of 1-5 above. GAP washing was proven to be able to increase %ee of enantio mixtures, e.g., 85% ee mixtures can be enhanced to >99%ee by GAP washing of solid crude products (not crystals from recrystalization, J. Org. Chem., 2013, 78, 4006−4012), which is against textbooks knowledge.

近期论文

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GAP Synthesis of Velcade, Dimeric Analogs, and Amino Compounds. Guigen Li, and Jian-bo Xie, U.S. Provisional Application No. 61/761,13, Feb 5, 2013. Highly Selective Domino Multi-Cyclizations for Forming Polycyclic Fused Acridines and Azaheterocyclic Skeletons; Bo Jiang, Xue Wang, Hai-Wei Xu, 1; Man-Su Tu, Shu-Jiang Tu, and Guigen Li, Org. Lett. 2013, 15, 1540-1543. N,N-Diisopropyl-N-phosphonyl Imines Lead to Efficient Asymmetric Synthesis of Aziridine-2-Carboxylic Esters, Padmanabha V. Kattamuri, Yiwen Xiong, Yi Pan and Guigen Li, submitted to Org. Biomol. Chem. 2013, 11, 3400 - 3408. Asymmetric C-C Bond Formation between Chiral N-Phosphonyl Imines and Ni(II)-Complex of Glycine Schiff Base Provides a GAP Synthesis of -syn-Diamino Acid Derivatives, Hao Sun, Haowei Zhang, Jianlin Han,Yi Pan and Guigen Li, Eur J. Org. Chem. 2013, 22, 4744-4747. Nanoparticle-based delivery system with oxidized phospholipids as target ligands for the prevention, diagnosis and treatment of atherosclerosis. Shu Wang, Guigen Li, Zhaoyang Fan, Patent Application, January 18, 2013, submitted. N,N-dichloro-4-methylbenzenesulfonamide [DICHLORAMINE T], Padmanabha V. Kattamuri, Guigen Li, The Encyclopedia of Reagents for Organic Synthesis [EROS], (Ed., D. Crich, John Wiley and Sons), 2013, in press. N,N-Dibromobenzenesulfonamide and N,N-Dibromo-p-toluenesulfonamide, Suresh Pindi & Guigen Li, The Encyclopedia of Reagents for Organic Synthesis [EROS], (Ed., D. Crich, John Wiley and Sons), 2013, in press. Radical Reactions in Domino Processes, Guanghui An and Guigen Li, "Domino Reactions - Concepts for Efficient Organic Synthesis" Chapter 5, Lutz Tietze, Ed., Wiley/VCH, in press. Domino Processes under Microwave Irradiation, High Pressure and in Water Bo Jiang, Shu-Jiang Tu and Guigen Li, "Domino Reactions - Concepts for Efficient Organic Synthesis" Chapter 5, Lutz Tietze, Ed., Wiley/VCH, in press. Design, synthesis and applications of new chiral N-2-phenyl-2-propyl sulfinylimines for Group-Assisted Purification (GAP) asymmetric synthesis, Suresh Pindi, Jianbin Wu and Guigen Li, J. Org. Chem. 2013, 76, 4006-4012. Regioselective multicomponent domino reactions providing rapid and efficient routes to fused acridines, Jin-Peng Zhang, Wei Fan, Jie Ding, Bo Jiang, Shu-Jiang Tu and Guigen Li HETEROCYCLES, in press. K2CO3/Ni(OAc)2 catalyzed aminobromination of β-methyl-β-nitrostyrenes with benzamide/ N,N-dibromobenzamide as nitrogen/bromine sources, Sheng Chen; Jianlin Han; Guigen Li; Yi Pan, Chinese J. of Chem. 2013, submitted. Highly diastereoselective aminobromination of -methyl--nitrostyrenes with t-butyl N,N-dibromocarbamate/t-butyl carbamate as bromine/nitrogen sources. Sheng Chen, Jianlin Han, Guigen Li, Yi Pan, Tetrahedron Lett, 2013, 54, 2781-84. Asymmetric Organocatalytic Strategy for Enantioenriched Tetrahydroquinoxaline Heterocycles. Feng Shi, Wei Tan, Qin Ye, Guan-Hua Ma, Shu-Jiang Tu and Guigen Li, xxxx, 2013, submitted. Four-Component [3+2+1]/[3+2] Bis-cyclization for Forming Cyclopenta-Fused Pyrazolo[3,4-b]pyridines, Bo Jiang, Qin Ye, Meng-Yuan Li, Shu-Liang Wang, Shu-Jiang Tu and Guigen Li, xxxx. submitted. Oxidative dehydrogenative couplings of pyrazol-5-amines selectively forming azopyrrole derivatives, Bo Jiang, Yi Ning, Shu-Jiang Tu and Guigen Li, xxxx. submitted. Metal-free [3+2+1]/[2+2+1] Biscyclization: Stereospecific Construction with Concomitant Functionalization of Indolizin-5(1H)-one, Tuan-jie Li, Hong-mei Yin, Zhong-qiu Liu,Chang-sheng Yao, Bo Jiang, Xiang-shan Wang, Shu-jiang Tu, Xiu-ling Li, Guigen Li, xxxx, submitted. Group-Assisted Purification (GAP) Chemistry in Velcade’s synthesis: asymmetric borylation of the imine with chiral phosphinyl auxiliary, Jian-Bo Xie, Jian Luo, Timothy R. Winn, David Cordes, Guigen Li, Beilstein J. Org. Chem. invited. Solution-phase-peptide synthesis (SoPPS) via the Group-Assisted Purification (GAP) chemistry without using chromatography and recrystallization, Jianbin Wu, Guanghui An, Siqi Lin, Jianbo Xie, Yi Pan and Guigen Li, xxxx, submitted. Asymmetric synthesis of α-alkenyl homoallylic primary amines via 1,2-addition of Grignard reagent to α,β-unsaturated phosphonyl imines, Yiwen Xiong, Haibo Mei, Chen Xie, Jianlin Han, Guigen Li and Yi Pan, xxxx, submitted.