A5101525659- Synthetic Organic Chemistry Methods
- N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
- Catalytic Cross-Coupling Reactions
- Chemical synthesis and alkaloids
- Catalytic C–H Functionalization Methods
- Synthesis and Properties of Aromatic Compounds
- Axial and Atropisomeric Chirality Synthesis
- Catalytic Alkyne Reactions
- Asymmetric Synthesis and Catalysis
- Traditional and Medicinal Uses of Annonaceae
- Crystallization and Solubility Studies
- X-ray Diffraction in Crystallography
- Alkaloids: synthesis and pharmacology
- Asymmetric Hydrogenation and Catalysis
- Supramolecular Chemistry and Complexes
- Chemical Synthesis and Reactions
- Surface Chemistry and Catalysis
- Synthesis of heterocyclic compounds
- Oxidative Organic Chemistry Reactions
- Molecular spectroscopy and chirality
- Advanced Synthetic Organic Chemistry
- Catalysis and Hydrodesulfurization Studies
- Cyclopropane Reaction Mechanisms
- Synthesis and Catalytic Reactions
- Sulfur-Based Synthesis Techniques
Beijing Normal University
2021-2025
University of Wisconsin–Madison
2018-2020
Tsinghua University
2015-2019
Indiana University School of Medicine
2016-2017
Lanzhou University
2010-2016
Lanzhou City University
2016
Center for Life Sciences
2015
Lanzhou Institute of Chemical Physics
2010-2012
Chinese Academy of Sciences
2010-2012
State Key Laboratory of Applied Organic Chemistry
2011
New antifungal drugs are urgently needed to address the emergence and transcontinental spread of fungal infectious diseases, such as pandrug-resistant Candida auris. Leveraging microbiomes marine animals cutting-edge metabolomics genomic tools, we identified encouraging lead molecules with in vivo efficacy. The most promising lead, turbinmicin, displays potent vitro mouse-model efficacy toward multiple-drug-resistant pathogens, exhibits a wide safety index, functions through fungal-specific...
Axial chirality widely exists in natural products, pharmaceutical compounds, and other functional molecules; these axially chiral compounds also find wide utility as catalysts or ligands organic synthetic chemistry. Nevertheless, whereas significant progress has been made toward the synthesis of enantioenriched molecules over past two decades, strategies involving organocatalysis have only started to emerge recently. N-heterocyclic carbene (NHC) organocatalysts recognized be powerful tools...
Abstract The dynamic kinetic resolution of 6‐hydroxypyranones with enals or alkynals through an asymmetric redox esterification is catalyzed by a chiral N‐heterocyclic carbene. resulting esters are obtained in good to high yields and levels enantio‐ diastereocontrol. reaction products further derivatized obtain functionalized sugar derivatives natural products.
Axially chiral molecules are among the most valuable substrates in organic synthesis. They typically used as ligands or catalysts asymmetric reactions. Recent progress for construction of these is mainly focused on transition-metal-catalyzed transformations. Here, we report enantioselective NHC-catalyzed (NHC: N-heterocyclic carbenes) atroposelective annulation cyclic 1,3-diones with ynals. In presence NHC precatalyst, base, Lewis acid and oxidant, a catalytic C-C bond formation occurs,...
Abstract The interrogation of complex biological pathways demands diverse small molecule tool compounds, which can often lead to important therapeutics for the treatment human diseases. Since natural products are most valuable source discovery therapeutics, derivatization has been extensively investigated generate molecules screenings. However, previous approaches only modified a limited number functional groups, resulted in skeleta. Here we show general strategy preparation library by...
N-Heterocyclic carbene (NHC) organocatalysis has been recognized as a powerful synthetic strategy for the construction of wide variety medicinally and biologically important molecules. Although NHCs are known umpolung aldehydes, NHC-based species involving non-umpolung processes have attracted considerable attention over past decade because their diverse reactivity applicability to asymmetric reactions. Previous reviews focused mainly on reactions α,β-unsaturated acyl azoliums, while current...
Abstract Planar-chiral cyclophanes have gained considerable concerns for drug discovery due to their unique conformational strain and 3D structure. However, the enantioselective synthesis of planar-chiral is a long-standing challenge synthetic community. We herein describe an N-heterocyclic carbene (NHC)-catalyzed asymmetric construction cyclophanes. This transformation occurs through dynamic kinetic resolution (DKR) process convert racemic substrates into macrocycle scaffolds in good high...
An N-heterocyclic carbene (NHC)-catalyzed atroposelective macrolactonization has been disclosed. This approach affords planar-chiral macrocycles in high yields with excellent enantioselectivities over a broad substrate scope. Controlled experiments suggest that the enantioselectivity might arise from cation–n interaction between acyl azolium and electron-rich moiety substrate. mechanism is supported by density functional theory calculations, which also an important π–π stabilizing transition state.
Macrocycles incorporating conformationally defined indoles are widely found in bioactive natural products. However, the catalytic enantioselective synthesis of planar-chiral via indolization involving macrocyclization remains elusive. Herein, we present first rhodium(III)-catalyzed atroposelective macrocyclization, which involves C-H activation aniline, and a subsequent oxidation [3 + 2] annulation reaction with an intramolecular alkyne. This protocol achieves construction indoles, planar...
Optically pure monosubstituted [n]paracyclophanes are promising candidates for material synthesis, asymmetric catalysis, and drug discovery. Thus far, only a few catalytic synthesis processes have been reported assessing these stained atropisomers. In this study, we describe highly enantioselective of by combining desymmetrization kinetic resolution. The proposed protocol involves Pd‐catalyzed atroposelective C–H bond olefination enabled monoprotected amino acid ligand, which affords variety...
The unprecedented N-heterocyclic carbene (NHC)-catalyzed intermolecular cross-coupling of enamides and aldehydes is described. Upon exposure to in the presence a NHC catalyst, catalytic C-C bond formation occurs, providing highly enantioselective N-protected amines, bearing quaternary carbon center, good yields with high enantioselectivities.
Abstract Planar‐chiral cyclophanes have received increasing attention for drug discovery and catalyst design. However, the catalytically asymmetric synthesis of planar‐chiral has been a longstanding challenge. We describe first Pd(II)‐catalyzed enantioselective C−H olefination prochiral cyclophanes. The low rotational barrier less hindered benzene ring in substrates allows reaction to proceed through dynamic kinetic resolution. This approach exhibits broad substrate scope, providing high...
Planar-chiral cyclophanes have received increasing attention for drug discovery due to their unique properties arising from the conformational strain. However, catalytic asymmetric synthesis of planar-chiral is one long-standing challenges in chemistry. We herein report a Brønsted acid-catalyzed transfer hydrogenation (ATH) reaction cyclophane-derived imines, providing good yields (up 98%) and with high enantioselectivities >99% ee). The mutable ansa bridge allows ATH occur through kinetic...
This review summarized the progress in synthesizing eight-membered N-heterocycles over past two decades (1995–2023), inspiring synthetic chemists to develop more efficient strategies for construction of these skeletons.
Going all the way: The first total synthesis of (±)-kopsihainanine A has been achieved in ten steps with a 12 % overall yield from commercially available 1,2,3,4-tetrahydrocarbazol-4-one (see scheme). This features an intramolecular conjugate addition iminium ion formed situ amide and substrate-controlled diastereoselective α-hydroxylation. Furthermore, ring D is by late-stage transannular SN2 reaction.
Abstract A highly efficient strategy for the formation of medium‐sized‐ring ethers and amines based on a gold‐catalyzed cascade reaction, involving enynyl ester isomerization intramolecular [3+2] cyclization, has been developed. Various multisubstituted unsaturated were obtained through this transformation. This method represents one relatively few transition metal catalyzed cycloaddition reactions medium‐sized ring synthesis.
Abstract The dynamic kinetic resolution of 6‐hydroxypyranones with enals or alkynals through an asymmetric redox esterification is catalyzed by a chiral N‐heterocyclic carbene. resulting esters are obtained in good to high yields and levels enantio‐ diastereocontrol. reaction products further derivatized obtain functionalized sugar derivatives natural products.
Abstract The planar chirality of macrocycles is a fascinating research topic. Locking the configurational flip between benzene ring and macrocycle leads to chirality, which can significantly enhance biological activity cyclophanes. Planar‐chiral cyclophanes are widely used in pharmaceuticals, chiral catalysts, functional materials. However, accessing planar‐chiral via asymmetric catalysis has remained challenging. Among various strategies, macrocyclization provides powerful tool for This...
Atroposelective synthesis of
<title>Abstract</title> <bold>Although chiral substituents have been incorporated into ansa chains to stabilize the</bold> <bold>conformations of cyclophanes and modulate the biological activities pharmaceuticals, asymmetric syntheses these atropisomers relies on substrate-induced diastereoselective macrocyclization. Consequently, enantio-, atrop-, macrocyclizations are yet be reported. Herein, we describe a N-heterocyclic carbene (NHC) phosphoric acid (CPA) dual-catalytic process for...
An Au-catalyzed tandem protocol involving enynyl ester isomerization and subsequent intramolecular [3 + 2] cyclization has been developed. This strategy provides an efficient approach for the synthesis of polyfunctional piperidines, which are subunits many bioactive molecules.
A concise synthesis of the tetracyclic core (ABCE rings) daphenylline has been accomplished involving a benzobicyclo[3.3.1] lactam as key intermediate. This bridged bicyclic intermediate was efficiently constructed via Brønsted acid promoted intramolecular Friedel-Crafts type Michael addition δ-benzyl α,β-unsaturated δ-lactam.
A concise asymmetric total synthesis of a fusarentin ether (1) with sequential biomimetic transformation to its analogues 6,7-dimethyl (2), 7-O-demethylmonocerin (3), and (+)-monocerin (4) has been accomplished. The cis-fused furobenzopyranones (3) were efficiently constructed via an intramolecular nucleophilic trapping quinonemethide intermediate, which was obtained by benzylic oxidation 6-methyl using hypervalent iodine reagent.