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1.
Chem Commun (Camb) ; 58(46): 6653-6656, 2022 Jun 08.
Artigo em Inglês | MEDLINE | ID: mdl-35593224

RESUMO

A Cu-catalyzed asymmetric 1,6-conjugate addition of in situ generated para-quinone methides (p-QMs) with ß-ketoester has been developed to construct a ketoester skeleton bearing an adjacent tertiary-quaternary carbon stereocenter in good yields and high enantioselectivities. This is the first example of metal-catalyzed asymmetric transformations of the in situ generated p-QMs, avoiding using pre-synthesized p-QMs requiring bulky 2,6-substitutions and highlighting a new dual catalytic activation with the chiral bis(oxazoline)-metal complex acting as a normal Lewis acid to activate the ß-ketoesters and a source of Brønsted acid responsible for generating the p-QMs in situ.


Assuntos
Cobre , Indolquinonas , Catálise , Metais
2.
Org Biomol Chem ; 19(30): 6588-6592, 2021 Aug 05.
Artigo em Inglês | MEDLINE | ID: mdl-34023869

RESUMO

Using visible light as a driving force and molecular oxygen as a green oxidant, we developed bis(oxazoline)-Ni(acac)2 catalyzed asymmetric α-hydroxylation of ß-keto esters under low photosensitizer loading, and the protocol enabled an efficient transformation to provide the desired chiral α-hydroxy-ß-keto esters in high yields (up to 99%) and enantioselectivities (up to 99% ee) at room temperature.

3.
J Org Chem ; 85(15): 9491-9502, 2020 Aug 07.
Artigo em Inglês | MEDLINE | ID: mdl-32692168

RESUMO

The functionalization of indoles in the carbocyclic ring has been achieved via organocatalytic enantioselective Friedel-Crafts benzhydrylation of hydroxyindoles with in situ generated ortho-quinomethanes in oil-water biphases, allowing an efficient access to varied diarylindolylmethanes with a wide substrate scope. The high yields, excellent stereoselectivities, mild conditions, low catalyst loading, and easy scalability also demonstrated the interest of this novel methodology.

4.
Org Biomol Chem ; 18(26): 4927-4931, 2020 07 08.
Artigo em Inglês | MEDLINE | ID: mdl-32573633

RESUMO

A highly enantioselective homogeneous fluorination of cyclic ß-keto esters catalyzed by diphenylamine linked bis(oxazoline)-Cu(OTf)2 complexes has been established in a continuous flow microreactor. The microreactor allowed an efficient transformation with reaction times ranging from 0.5 to 20 min, and the desired products were afforded in high yields (up to 99%) with excellent enantioselectivities (up to 99% ee) at a low catalyst loading of 1 mol%.

5.
Org Biomol Chem ; 18(13): 2398-2404, 2020 04 01.
Artigo em Inglês | MEDLINE | ID: mdl-32191253

RESUMO

A highly regioselective and enantioselective N-alkylation of isoxazol-5-ones with para-quinone methides promoted by bi-functional squaramide catalysts was developed. This unexpected asymmetric N-addition of isoxazolinones afforded a series of enantioenriched N-diarylmethane substituted isoxazolinones with high yields and enantioselectivities (up to 97 : 3 er). This reaction not only provides a useful approach for intermolecular chiral C-N bond formation but also demonstrates the immense potential of isoxazol-5-ones as N-nucleophiles in catalytic asymmetric reactions.

6.
Front Biosci ; 11: 2113-22, 2006 Sep 01.
Artigo em Inglês | MEDLINE | ID: mdl-16720298

RESUMO

Metallothionein (MT), a metal-binding protein induced primarily by heavy metals in vertebrates, is considered a biomarker for environmental heavy-metal contamination. To investigate heavy metal pollution in the freshwater environment, MT-I and MT-II were purified from livers of crucian carp (Carassius carassius) by gel exclusion chromatography and ion exchange chromatography. To detect the purified MT-II, a specific monoclonal antibody (mAb) against crucian carp MT-II was produced from the hybridoma strains by cell-cell fusion. By using Enzyme-Linked Immunosorbent Assay (ELISA) with this mAb, the purified crucian carp MT-II was detected with a high specificity and sensitivity. There was a good correlation between the amount of MT-II in carp livers and the concentration of heavy metals in water. ELISA was then used to evaluated the degree of heavy metal pollution in two freshwater systems. The results indicate that the MT-II content in carp liver tissue can be used as an indicator of environmental heavy-metal pollution.


Assuntos
Biomarcadores/análise , Ensaio de Imunoadsorção Enzimática/métodos , Metalotioneína/análise , Metais Pesados/análise , Poluentes da Água/análise , Animais , Anticorpos Monoclonais , Carpas , Monitoramento Ambiental/métodos , Fígado/química , Metalotioneína/metabolismo , Metais Pesados/metabolismo , Espectrofotometria Atômica , Poluentes da Água/metabolismo
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