A5025795535- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Asymmetric Synthesis and Catalysis
- Catalytic C–H Functionalization Methods
- Synthesis and Catalytic Reactions
- Synthetic Organic Chemistry Methods
- Oxidative Organic Chemistry Reactions
- Asymmetric Hydrogenation and Catalysis
- Radical Photochemical Reactions
- Chemical Synthesis and Analysis
- Sulfur-Based Synthesis Techniques
- Microbial Natural Products and Biosynthesis
- Crystallography and molecular interactions
- Vanadium and Halogenation Chemistry
- Chemical synthesis and alkaloids
- Chemical Reactions and Isotopes
- Catalytic Cross-Coupling Reactions
- Chemical Synthesis and Reactions
- Bioactive natural compounds
- Molecular spectroscopy and chirality
- Advanced Synthetic Organic Chemistry
- Biological Activity of Diterpenoids and Biflavonoids
- Molecular Spectroscopy and Structure
- Click Chemistry and Applications
- Plant chemical constituents analysis
National University of Singapore
2019-2022
Republic Polytechnic
2020
New York University
2017-2018
Sichuan University
2010-2017
Chengdu University
2017
Lanzhou University
2011
Abstract The dehydrogenative alkenylation of C-H bonds with alkenes represents an atom- and step-economical approach for olefin synthesis molecular editing. Site-selective alkanes aldehydes the substrate as limiting reagent holds significant synthetic value. We herein report a photocatalytic method direct aryl in absence any external oxidant. A diverse range commodity feedstocks pharmaceutical compounds are smoothly alkenylated useful yields partner reagent. late-stage complex molecules...
Abstract Enantioenriched 1,4‐dicarbonyl compounds are versatile synthons in natural product and pharmaceutical drug synthesis. We herein report a mild pathway for the efficient enantioselective synthesis of these directly from aldehydes through synergistic cooperation between neutral eosin Y hydrogen atom transfer photocatalyst chiral rhodium Lewis acid catalyst. This method is distinguished by its operational simplicity, abundant feedstocks, economy, ability to generate products high yields...
A new 1,3-dipolar cycloaddition of nitrile imines with 3-alkenyl-oxindoles was catalyzed by a chiral Mg(ClO(4))(2) complex an N,N'-dioxide ligand. The reaction is so far the sole catalytic synthesis spiro-pyrazoline-oxindole derivatives. wide variety substrates were explored to obtain good yields (up 98%) and excellent enantioselectivities 99%). This expands scope propargyl anion type 1,3-dipole in construction 2-pyrazoline subunit.
Deuterium labelled compounds are of significant importance in chemical mechanism investigations, mass spectrometric studies, diagnoses drug metabolisms, and pharmaceutical discovery. Herein, we report an efficient hydrogen deuterium exchange reaction using oxide (D2O) as the source, enabled by merging a tetra-n-butylammonium decatungstate (TBADT) atom transfer photocatalyst thiol catalyst under light irradiation at 390 nm. This deuteration protocol is effective with formyl C-H bonds wide...
A reductive dicarbofunctionalization of alkenes has been developed and applied to the preparation substituted carbo- heterocycles.
The first iron(III)/N,N'-dioxide-catalyzed asymmetric haloamination of 3-alkylidene- and 3-arylidene-indolin-2-ones was developed, affording the corresponding chiral oxindole derivatives bearing vicinal haloamine substituents with excellent results (up to 99% yield, ee, >19 : 1 dr). This iron catalyst also exhibits perfect enantioselectivity for chalcone derivatives. cooperative activation substrate reagent in concert guarantees high stereoselectivity.
A catalytic asymmetric conjugate allylation was successfully developed to synthesize potential pharmacologically active 4-allyl-2-oxochroman skeletons. dual activation strategy employed by using N,N'-dioxide-Yb(OTf)(3) activate coumarins and (CuOTf)(2)•C(7)H(8) tetraallyltin via transmetalation, respectively. Good yields enantioselectivities were obtained under mild conditions.
The asymmetric Darzens reaction between phenacyl bromides and N-protected isatins was developed to synthesize potentially bioactive spiro-epoxyoxindoles. optically active products were obtained in moderate good yields enantioselectivities catalyzed by chiral N,N′-dioxide-Co(acac)2 complexes. A retro-aldol process accompanying the ring-closure step observed process. control determined be initial aldol addition.
A diastereodivergent asymmetric cascade Michael-alkylation by switching the alkylation step of intramolecular trapping aza-<italic>ortho</italic>-xylylene intermediate or direct S<sub>N</sub>2 substitution has been developed.
A highly diastereo- and enantioselective hetero-Diels–Alder (HDA) reaction of a Brassard-type diene with aliphatic aldehydes has been developed. The chiral N,N′-dioxide L2/In(OTf)3 complex was efficient toward the obtention corresponding β-methoxy-γ-methyl α,β-unsaturated δ-lactones in good yields (up to 86%) as well dr ee values 97:3 cis/trans 94% ee). In addition, product 4a could be easily transformed into methyl-protected epi-prelactone B by hydrogenation.
The N,N'-dioxide-Cu(OTf)(2) complexes were applied in the asymmetric amination reaction of N-acetyl enamides with dialkyl azodicarboxylate, giving corresponding products good yields high enantioselectivities (up to 91% ee). Precursors vicinal diamine readily obtained excellent diastereoselectivities (>95:5) by NaBH(4) reduction.
The first catalytic asymmetric hetero-Diels-Alder reaction of Brassard's dienes with isatins was realized using Mg(II)/N,N'-dioxide complexes as catalysts, affording the corresponding chiral spirolactones bearing tetrasubstituted centers in up to 99% yield ee and >99 : 1 dr within 3 hours. In mechanism, based on operando IR experiments, a predominant Diels-Alder pathway found reaction. A possible transition state model also proposed.
Eine chirale Lewis-Säure vermittelt die elektrophile Addition und Arylumlagerung in der Titelreaktion. Die Produkte einfachen C3-Arylierung, ein quartäres Kohlenstoffstereozentrum enthalten, werden hoch enantioselektiv gebildet. As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed may be re-organized for online delivery, but not copy-edited or typeset. Technical support issues arising from (other than...
Abstract Enantioenriched 1,4‐dicarbonyl compounds are versatile synthons in natural product and pharmaceutical drug synthesis. We herein report a mild pathway for the efficient enantioselective synthesis of these directly from aldehydes through synergistic cooperation between neutral eosin Y hydrogen atom transfer photocatalyst chiral rhodium Lewis acid catalyst. This method is distinguished by its operational simplicity, abundant feedstocks, economy, ability to generate products high yields...
Catalyzed oxidative C-C bond coupling reactions play an important role in the chemical synthesis of complex natural products medicinal importance. However, poor functional group tolerance renders them unfit for naturally occurring polyphenolic flavones. We find that molecular oxygen alkaline water acts as a hydrogen atom acceptor and oxidant catalyst-free (without added catalyst) luteolin other By this facile method, we achieve small collection flavone dimers trimers including dicranolomin,...
Cooperative catalysis: An easily available new type of primary–secondary diamine was synthesized as a highly efficient bifunctional catalyst in the asymmetric crossed-conjugate addition β,β-dialkyl nitroalkenes to α,β-unsaturated acyclic or cyclic ketones for first time. The wide substrate scope, excellent yield (up 96 %) and enantioselectivity 99 % enantiomeric excess (ee)) under mild reaction conditions provides potential method formation allylic nitro compounds (see scheme). Detailed...
Abstract The comprehensive investigation of target interactions from native cellular environments is paramount importance for natural products and related bioactive compounds in drug discovery chemical biology. Current chemoproteomic tools, such as situ proteome profiling can do so effectively, but rely heavily on “tagged” probes that are accessible through traditional organic synthesis at the reactive sites a compound, which may often be required binding. Late‐stage functionalization...
The authors describe a catalytic system for the asymmetric conjugate allylation of coumarins, furnishing corresponding 4-allyl-2-oxochroman derivatives in high yield and enantioselectivity.
Abstract The scalable method is applicable to a broad range of arylated oxindoles and diaryliodonium salts with high excellent enantioselectivity.
Abstract The asymmetric Darzens reaction of phenacyl bromides and N‐protected isatins provides various spiro‐epoxyindoles.
Abstract The title reaction affords chiral spirolactones (III) and (V) bearing tetrasubstituted centers in high yields stereoselectivities (up to 99% e.e.).