Taoda Shi

ORCID: 0000-0002-4250-3779
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Research Areas
  • Cyclopropane Reaction Mechanisms
  • Crystallization and Solubility Studies
  • X-ray Diffraction in Crystallography
  • Asymmetric Synthesis and Catalysis
  • Catalytic C–H Functionalization Methods
  • Synthetic Organic Chemistry Methods
  • Asymmetric Hydrogenation and Catalysis
  • Synthesis and Biological Evaluation
  • Catalytic Alkyne Reactions
  • Synthesis and Catalytic Reactions
  • Multicomponent Synthesis of Heterocycles
  • Chemical Synthesis and Analysis
  • Click Chemistry and Applications
  • Crystallography and molecular interactions
  • Heat shock proteins research
  • Endoplasmic Reticulum Stress and Disease
  • Protein Tyrosine Phosphatases
  • Cancer, Hypoxia, and Metabolism
  • N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
  • Enzyme Structure and Function
  • Oxidative Organic Chemistry Reactions
  • Synthesis and biological activity
  • Sulfur-Based Synthesis Techniques
  • Radical Photochemical Reactions
  • Biochemical and Molecular Research

Sun Yat-sen University
2019-2024

Yantai University
2024

University of Arizona
2016-2022

East China Normal University
2009-2019

Sichuan University
2011

A highly enantioselective Strecker reaction of difluoromethyl and trifluoromethyl ketoimines was developed. Remarkable fluorine effect on the reactivity selectivity is observed discussed.

10.1021/ol201316z article EN Organic Letters 2011-06-30

A one-pot tandem Wittig/conjugate reduction/Paal-Knorr reaction is reported for the synthesis of di- or trisubstituted furans. This novel sequence first demonstrates possibility successively recycling waste from upstream steps to catalyze downstream reactions.

10.1021/acs.orglett.5b00442 article EN Organic Letters 2015-03-02

Pd( ii )-catalyzed auto-tandem formal [4+1] cycloaddition of diazoacetates and aryl propargyl alcohols affords 2,5-dihydrofurans as the dominant product over traditional ones.

10.1039/c5cc05000f article EN Chemical Communications 2015-01-01

A metal-free tandem Friedel-Crafts/lactonization reaction to 3,3-diaryl or 3-alkyl-3-aryl benzofuranones catalyzed by HClO(4) was reported. variety of tertiary α-hydroxy acid esters could readily react with substituted phenols afford the desired products in rich diversity. The synthetic utility demonstrated synthesis polycyclic compounds. (1)H NMR studies supported that this proceeded via sequence.

10.1021/jo300395x article EN The Journal of Organic Chemistry 2012-03-29

Abstract An elegant synergistic catalytic system comprising a ruthenium complex with chiral Brønsted acid was developed for four‐component Mannich/cascade aza‐Michael reaction. The ruthenium‐associated ammonium ylides successfully trapped in situ generated imines indicates stepwise process of proton transfer the ruthenium‐catalyzed carbenoid NH insertion different decomposition abilities various complexes towards diazo compounds were well explained by calculated thermodynamic data....

10.1002/chem.201304576 article EN Chemistry - A European Journal 2014-01-16

We report a green synthesis of spiro[2,3-dihydrofuran-3,3′-oxindole] derivatives which are potential value in medicinal chemistry.

10.1039/c9gc01751h article EN Green Chemistry 2019-01-01

An enantioselective cyclization of diazoindolinones with o-hydroxymethyl chalcones has been established by a cooperative dirhodium complex and chiral phosphonic acid catalysis under mild conditions. This reaction is the first example catalytic asymmetric intramolecular Michael-type trapping oxonium ylide enabled phosphoric through dual H-bonding activation model, which provides an efficient access to spirochroman-3,3-oxindoles, vicinal quaternary tertiary stereocenters, in good excellent...

10.1021/acs.orglett.0c00587 article EN Organic Letters 2020-04-01

An enantioselective intermolecular Mannich-type interception of phenolic oxonium ylides with imines has been developed. The cooperative catalysis achiral dirhodium complex and chiral phosphoric acid introduced to circumvent the competitive O–H bond insertion via dual H-bonding, enabling synthesis enantioenriched 2,2-disubstituted dihydrobenzofurans good high yield excellent enantioselectivity under mild conditions. Preliminary antitumor activity study these generated products indicated that...

10.1021/acscatal.1c01321 article EN ACS Catalysis 2021-05-29

This study introduces a novel approach for synthesizing Benzoxazine-centered Polychiral Polyheterocycles (BPCPHCs) via an innovative asymmetric carbene-alkyne metathesis-triggered cascade. Overcoming challenges associated with intricate stereochemistry and multiple chiral centers, the catalytic Carbene Alkyne Metathesis-mediated Cascade (CAMC) is employed using dirhodium catalyst/Brønsted acid co-catalysis, ensuring precise stereo control as validated by X-ray crystallography. Systematic...

10.1002/anie.202401189 article EN Angewandte Chemie International Edition 2024-03-20

Reduce your waist: A highly efficient synthesis of α-CF3 γ-keto esters and trifluoromethylated 4,5-dihydro pyridazinones is reported based on tandem Wittig–conjugate reduction reactions, which directly utilize the Ph3PO waste from Wittig reaction as Lewis base catalyst to activate HSiCl3 for chemoselective conjugate reduction. As a service our authors readers, this journal provides supporting information supplied by authors. Such materials are peer reviewed may be re-organized online...

10.1002/asia.201201130 article EN Chemistry - An Asian Journal 2013-01-10

A highly efficient three-component reaction of α-diazo ester, water and isatin was developed by using CuSO4 as the catalyst. In this reaction, used both a reactant solvent. With environmentally benign economical protocol, series 3-hydroxyindolin-2-one derivatives were efficiently produced in good yields with moderate to high diastereoselectivities.

10.1039/c2gc36708d article EN Green Chemistry 2012-12-18

Dual to the death: Catalyzed by [Rh2(OAc)4] and a chiral phosphoric acid, an enantioselective symmetric three-component reaction of diazo compounds with imines water is reported give β-amino-α-hydroxy acid derivatives in good yield (up 86 %) excellent diastereoselectivity 98:2 d.r.) enantioselectivity 97 % ee). Detailed facts importance specialist readers are published as "Supporting Information". Such documents peer-reviewed, but not copy-edited or typeset. They made available submitted...

10.1002/cctc.201000437 article EN ChemCatChem 2011-01-25

Abstract A rhodium‐catalyzed formal [4+1]‐cycloaddition of pyridotriazoles and aryl propargyl alcohols is reported, providing an effective access to 2‐pyridyl‐substituted 2,5‐dihydrofuran derivatives in moderate high yields. Mechanistically, the proposed oxonium ylide intermediate this catalytic alkyne carbocyclization transformation verified by interception experiment for first time. magnified image

10.1002/adsc.201801497 article EN Advanced Synthesis & Catalysis 2019-01-05

We herein reported a sustainable synthesis of 3,3-disubstituted oxindoles via Michael-type reaction based on the CuBr-catalysed capture carboxylic oxonium ylides with isatylidene malononitrile. The is characterized by high atom economy and low economic constraints. catalyst CuBr could be conveniently recyclized. products were found to inhibitory against Na ion channels. expect shed light biologically interesting molecules directed principles green chemistry.

10.1016/j.gresc.2023.04.006 article EN cc-by-nc-nd Green Synthesis and Catalysis 2024-08-01

Through the addition of chlorine atoms to aromatic ring 10(11)-dehydrocurvularin, covalent inhibition was tuned for p97 selectivity relative proteasome.

10.1039/c6ob00560h article EN Organic & Biomolecular Chemistry 2016-01-01

Water and ethyl diazoacetate were found to be matched components for generating highly reactive nucleophilic oxonium ylide in the presence of a dirhodium acetate catalyst. Simultaneous trapping intermediate with aryl imines gave β-aryl isoserine derivatives high diastereoselectivity.

10.1039/b915013g article EN Organic & Biomolecular Chemistry 2009-01-01

A highly diastereoselective approach for the rapid construction of an isochroman skeleton was achieved by copper(<sc>ii</sc>)-catalyzed transformation alcohol-tethered enones and diazo compounds.

10.1039/c8cc06390g article EN Chemical Communications 2018-01-01

Zwei Wege stehen der Titelreaktion offen, je nachdem, in welcher Reihenfolge die Substrate zugegeben werden. Auf divergente Weise entstehen mehrfach funktionalisierte Produkte – Pyrrolidine oder lineare α-Aminoester-Derivate guten Ausbeuten und mit hohen Diastereoselektivitäten.

10.1002/ange.201303987 article DE Angewandte Chemie 2013-07-03

Paclitaxel (Taxol@) as a cornerstone of chemotherapy remains in high demand. The semi-synthesis paclitaxel via coupling Taxus leaf-produced baccatin III and manually synthesized isoserine (C-13 side chain) is one the solutions to avoid environmental damage caused by sacrifice whole brevifolia. A green synthesis C-13 chain pivotal production paclitaxel. We herein report derivatives straightforward assembly isoserines based on an Rh2(TPA)3(OAc)/CPA1 co-catalyzed asymmetric multi-component...

10.1016/j.gresc.2022.05.008 article EN cc-by-nc-nd Green Synthesis and Catalysis 2022-05-23

The blockade of A2A adenosine receptor (A2AAR) activates immunostimulatory response through regulating signaling in tumor microenvironment. Thus, A2AAR has been proposed as a promising target for cancer immunotherapy. In this work, we designed new series benzo[4,5]imidazo[1,2-a]pyrazin-1-amine derivatives bearing an amide substitution at 3-position to obtain potent antitumor antagonist vivo. structure–activity relationship studies were performed by molecular modeling and radioactive assay....

10.1021/acs.jmedchem.2c00101 article EN Journal of Medicinal Chemistry 2022-06-17

We report a bifunctional Ag catalyst promoted intramolecular capture of oxonium ylides with alkynes for the enantioselective synthesis 2,5-dihydrofurans.

10.1039/c9ob01903k article EN Organic & Biomolecular Chemistry 2019-01-01
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