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1.
J Org Chem ; 89(2): 928-938, 2024 Jan 19.
Artigo em Inglês | MEDLINE | ID: mdl-38181049

RESUMO

Chiral diarylmethylamides are a privileged skeleton in many bioactive molecules. However, the enantioselective synthesis of such molecules remains a long-standing challenge in organic synthesis. Herein, we report a chiral bifunctional squaramide catalyzed asymmetric aza-Michael addition of amides to in situ generated ortho-quinomethanes, affording enantioenriched diarylmethylamides in good yields with excellent enantioselectivities. This work not only provides a new strategy for the construction of the diarylmethylamides but also represents the practicability of amides as nitrogen-nucleophiles in asymmetric organocatalysis.

2.
J Org Chem ; 89(2): 975-985, 2024 Jan 19.
Artigo em Inglês | MEDLINE | ID: mdl-38181067

RESUMO

Enantioselective synthesis of eight-membered N-heterocycles represents a long-standing challenge in organic synthesis. Here, by combining the squaramide and DBU catalysis, a sequential asymmetric conjugate addition/cyclization reaction between benzofuran-derived azadienes and ynones has been well-developed, providing straightforward access to chiral eight-membered N-heterocycles in high yields with stereoselectivities. This protocol features the use of a bifunctional squaramide catalyst for controlling the enantioselectivity of products, while the DBU is utilized to achieve intramolecular cyclization and improve the diastereoselectivity of products.

3.
Chem Commun (Camb) ; 59(57): 8822-8825, 2023 Jul 13.
Artigo em Inglês | MEDLINE | ID: mdl-37357694

RESUMO

A sequential asymmetric conjugate addition/cyclisation of α-bromohydroxamates with para-quinone methide derivatives has been developed, which provides enantioenriched 1,4-benzoxazepines in generally high yields (up to 95%) and good enantioselectivities (up to 97 : 3 er). This protocol not only offers a novel and straightforward strategy for constructing chiral 1,4-benzoxazepines, but also demonstrates the potential of α-bromohydroxamates as three-atom synthons in asymmetric cyclisation reactions.


Assuntos
Indolquinonas , Estereoisomerismo , Ciclização
4.
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
5.
Org Lett ; 23(7): 2471-2476, 2021 Apr 02.
Artigo em Inglês | MEDLINE | ID: mdl-33733793

RESUMO

A sequential enantioselective conjugate addition/hydroalkoxylation between in situ generated ortho-quinomethanes and ynones by combining bifunctional squaramide and DBU catalysis has been developed. A variety of eight-membered cyclic ethers with two contiguous tertiary stereocenters were obtained in high yields with excellent stereoselectivities. This reaction not only provides a new strategy for constructing enantioenriched eight-membered cyclic ethers but also demonstrates the practicability of ynones as C4-syntons for the synthesis of chiral medium-membered rings.

6.
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.

7.
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%.

8.
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.

9.
Org Biomol Chem ; 16(41): 7702-7710, 2018 11 07.
Artigo em Inglês | MEDLINE | ID: mdl-30288521

RESUMO

A highly enantioselective fluorination of indanone-2-carboxylates catalyzed by a polystyrene-supported diphenylamine-linked bis(oxazoline) (PS-box)-Cu(OTf)2 complex has been developed in a continuous flow system. The supported complex exhibited extremely efficient catalytic performance with high activity, affording the corresponding products in excellent yields (up to 99% yield) with excellent enantioselectivities (up to 99% ee) and more than 4000 turnover number (TON).

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