A5021801739- Asymmetric Synthesis and Catalysis
- Axial and Atropisomeric Chirality Synthesis
- Chemical Synthesis and Reactions
- Sulfur-Based Synthesis Techniques
- Synthetic Organic Chemistry Methods
- Synthesis and Catalytic Reactions
- Asymmetric Hydrogenation and Catalysis
- Molecular Sensors and Ion Detection
- Chemical Synthesis and Analysis
- Luminescence and Fluorescent Materials
- Vanadium and Halogenation Chemistry
- Polyoxometalates: Synthesis and Applications
- Oxidative Organic Chemistry Reactions
- RNA Interference and Gene Delivery
- Click Chemistry and Applications
- Advanced Synthetic Organic Chemistry
- Sulfur Compounds in Biology
- Chemical Reactions and Isotopes
- Advanced biosensing and bioanalysis techniques
- Catalytic C–H Functionalization Methods
- Fluorine in Organic Chemistry
- Organophosphorus compounds synthesis
- Ferroptosis and cancer prognosis
- Synthesis and Reactivity of Sulfur-Containing Compounds
- Organic Chemistry Cycloaddition Reactions
Xiamen University
2019-2025
Target (United States)
2025
University of Geneva
2017-2020
NCCR Chemical Biology - Visualisation and Control of Biological Processes Using Chemistry
2017-2019
Southeast University
2019
Nanyang Technological University
2014-2017
National University of Singapore
2011-2012
Nanjing University
2007-2010
Jilin Agricultural University
2010
Wenzhou University
2007
Abstract We report halogenated pentanidiums as phase‐transfer catalysts for the asymmetric alkylation of sulfenate anions to various sulfoxides with high enantioselectivities (up 99 % ee ) and yields %). This approach gives access enantioenriched heterocyclic that might not be compatible strong oxidants or organometallic reagents. Computational studies have revealed multiple noncovalent interactions such halogen bonds nonclassical hydrogen are involved.
ConspectusCatalysts accelerate biological processes and organic reactions in a controlled selective fashion. There are continuing efforts asymmetric catalysis to develop efficient catalysts with broad reaction scope industrial practicability. Among the various modes of catalysis, phase-transfer has attracted intense interest due its facile scale up low catalyst loading. Chiral quaternary ammonium phosphonium salts well-studied classes chiral catalysts, they typically composed sp3-hybridized...
A new chiral entity, pentanidium, has been shown to be an excellent phase-transfer catalyst. The enantioselective Michael addition reactions of tert-butyl glycinate-benzophenone Schiff base with various α,β-unsaturated acceptors provide adducts high enantioselectivities. successful gram-scale experiment at a low catalyst loading 0.05 mol % indicates the potential for practical applications this methodology. Phosphoglycine ester analogues can also utilized as donor, affording enantioenriched...
The induction of ferroptosis is promising for cancer therapy. However, the mechanisms enabling cells to evade ferroptosis, particularly in low-cystine environments, remain elusive. Our study delves into intricate regulatory Activating transcription factor 3 (ATF3) on Cystathionine β-synthase (CBS) under cystine deprivation stress, conferring resistance colorectal (CRC) cells. Additionally, our findings establish a positively correlation between this signaling axis and CRC progression,...
Chiral anion-controlled ion-pairing catalysis was demonstrated to be a wide-ranging strategy that can utilize variety of cationic metal species. In similar manner, we envision complementary using chiral cation in partnership with inorganic anionic salts. Herein, report dicationic bisguanidinium-catalyzed asymmetric oxidation reaction alkenes potassium permanganate. induction is attributed interaction between and enolate anion. The success the current permanganate together mechanistic...
The disulfide dihedral angle in epidithiodiketopiperazines (ETPs) is near 0°. Application of this highest possible ring tension to strain-promoted thiol-mediated uptake results efficient delivery the cytosol and nucleus. Compared previous best asparagusic acid (AspA), ring-opening exchange with ETPs occurs more efficiently even nonactivated thiols, resulting thiols rapidly disulfides. ETP-mediated cellular than 20 times compared AspA, without endosomal capture, depends on temperature,...
Most asymmetric phase transfer reactions are Brønsted base reactions, and the inorganic bases used greatly influenced profile of reaction. Alkoxide salts able to activate substrates with high pKa values, but background often unavoidable. On other hand, carbonate phosphate milder, their low basicity limits scope reactions. This presents a difficult situation whereby fragile such as lactone will be hydrolyzed by stronger not activated weaker one. Thus, probase strategy is devised, in which...
The first enantioselective tungstate-catalyzed oxidation reaction is presented. High enantioselectivities were achieved for a variety of drug-like phenyl and heterocyclic sulfides under mild conditions with H2 O2 , cheap environmentally friendly oxidant. Synthetic utility was demonstrated through the preparation (S)-Lansoprazole, commercial proton-pump inhibitor. active ion-pair catalyst identified to be bisguanidinium diphosphatobisperoxotungstate using Raman spectroscopy computational studies.
Abstract Catalytic use of peroxomolybdate for asymmetric transformations has attracted increasing attention due to its catalytic properties and application in catalysis. Herein, we report chiral bisguanidinium dinuclear oxodiperoxomolybdosulfate [ BG ] 2+ [(μ-SO 4 )Mo 2 O (μ-O ) (O 2− ion pair, as a catalyst enantioselective sulfoxidation using aqueous H the terminal oxidant. The pair is isolatable, stable useful oxidation range dialkyl sulfides. practical utility was illustrated gram-scale...
Cyclic oligochalcogenides (COCs) are emerging as promising systems to penetrate cells. Clearly better than and different the reported diselenolanes epidithiodiketopiperazines, we introduce benzopolysulfanes (BPS), which show efficient delivery, insensitivity inhibitors of endocytosis, compatibility with substrates large proteins. This high activity coincides reactivity, selectively toward thiols, exceeding exchange rates disulfides under tension. The result is a dynamic-covalent network...
The emerging power of thiol-mediated uptake with strained disulfides called for a move from sulfur to selenium. We report that according results fluorescent model substrates, cellular 1,2-diselenolanes exceeds 1,2-dithiolanes and epidithiodiketopiperazines regard efficiency as well intracellular localization. diselenide analog lipoic acid performs best. This 1,2-diselenolane delivers fluorophores efficiently the cytosol HeLa Kyoto cells, without detectable endosomal capture or dominant...
Ellman's reagent has caused substantial confusion and concern as a probe for thiol-mediated uptake because it is the only established inhibitor available but works neither efficiently nor reliably. Here we use fluorescent cyclic oligochalcogenides that enter cells by to systematically screen more potent inhibitors, including epidithiodiketopiperazines, benzopolysulfanes, disulfide-bridged γ-turned peptides, heteroaromatic sulfones thiosulfonates, thiosulfinates disulfides. With nanomolar...
Chiral cyclic sulfoxides are valuable heterocyclic building blocks in natural products and pharmaceutically active molecules as well optoelectronics materials. In view of their manifold applications but limited number available synthetic methodologies to obtain them, highly enantioselective catalytic approaches access chiral therefore desired. Here, a sustainable oxidation sulfides has been developed by employing situ-generated bisguanidinium peroxomolybdate ion-pairing catalysis. bearing...
Chiral conjugated polymers P-1 and P-2 were synthesized by the polymerization of (S)-6,6'-di(4-methylphenyl)-3,3'-diiodo-2,2'-bisoctoxy-1,1'-binaphthyl (S-M-2) (S)-6,6'-dibromo-3,3'-di(4-methylphenyl)-2,2'-bisoctoxy-1,1'-binaphthyl (S-M-3) with 5,5'-divinyl-2,2'- bipyridine (M-1) under Heck cross-coupling reaction, respectively. The chiral can show strong blue-green fluorescence. responsive properties on transition metal ions H+ investigated fluorescent spectra. Cu2+ Ni2+ lead to nearly...
Abstract We report halogenated pentanidiums as phase‐transfer catalysts for the asymmetric alkylation of sulfenate anions to various sulfoxides with high enantioselectivities (up 99 % ee ) and yields %). This approach gives access enantioenriched heterocyclic that might not be compatible strong oxidants or organometallic reagents. Computational studies have revealed multiple noncovalent interactions such halogen bonds nonclassical hydrogen are involved.
A pentanidium-catalyzed highly enantioselective conjugate addition of 3-alkyloxindoles to phenyl vinyl sulfone has been demonstrated. This approach allows the construction 3,3-dialkyl-substituted oxindole frameworks with high yield and excellent enantioselectivity (up 99%) under simple phase-transfer conditions. variety oxindoles bearing all-carbon quaternary stereogenic centers were obtained in presence 0.25 mol% pentanidium. Meanwhile, practicality was illustrated by a gram-scale...
Cyclic oligochalcogenides are emerging as powerful tools to penetrate cells. With disulfide ring tension maximized, selenium chemistry had be explored next enhance speed and selectivity of dynamic covalent exchange on the way into cytosol. We show that diseleno lipoic acid (DiSeL) delivers a variety relevant substrates. DiSeL-driven uptake artificial metalloenzymes enables bioorthogonal fluorophore uncaging within Binding bicyclic peptide, phalloidin, actin fibers evinces targeted delivery...
Neutral halogen bonding donors (XBDs) containing sp3-hybridized carbon–bromine and sulfoxide moieties were designed synthesized. They promoted quinolines imines reduction easily with a relatively low catalyst loading (5 mol %). Their strengths quantified using 31P NMR spectroscopy molecular electrostatic potential (MESP) analysis. Single-crystal X-ray analysis unambiguously confirmed the presence of intramolecular C(sp3)–Br···H–N hydrogen within amide-derived XBD. Combined experimental...
A catalytic enantioselective synthesis of bicalutamide derivatives with promising potentials in prostate cancer treatment has been disclosed. The key intermediates, α-hydroxy-β-keto esters, were efficiently constructed through cinchoninium-mediated asymmetric oxohydroxylation easily accessible alkenes potassium permanganate. Good yields and high levels induction are achieved. This method provides a new synthetic route to analogues structural diversity, which will beneficially support...
Abstract A pentanidium‐catalyzed highly enantioselective conjugate addition of 3‐alkyloxindoles to phenyl vinyl sulfone has been demonstrated. This approach allows the construction 3,3‐dialkyl‐substituted oxindole frameworks with high yield and excellent enantioselectivity (up 99 %) under simple phase‐transfer conditions. variety oxindoles bearing all‐carbon quaternary stereogenic centers were obtained in presence 0.25 mol % pentanidium. Meanwhile, practicality was illustrated by a...