Synthesis of axially chiral biaryl thioglycosides through thiosugar-directed Pd-catalyzed asymmetric C-H activation

Maha Fatthalla; Nicolas Grimblat; Etienne Brachet; Mouad Alami; Vincent Gandon; Franck Le Bideau; Samir Messaoudi

doi:10.1039/d1cc03971g

Synthesis of axially chiral biaryl thioglycosides through thiosugar-directed Pd-catalyzed asymmetric C-H activation

Maha Fatthalla
, Nicolas Grimblat
, Etienne Brachet
, Mouad Alami
, Vincent Gandon
, Franck Le Bideau
, Samir Messaoudi

Faculty of Science
Université Paris-Saclay
Universidad Nacional de Rosario
Laboratoire de Probabilités et Modèles Aléatoires

Résultats de recherche: Contribution à un journal › Article › Revue par des pairs

Résumé

Herein we report for the first time that the thiosugar moiety can be used both as a directing group enabling the regioselective activation of a C-H bond of biaryl scaffolds and as a chiral source inducing axial chirality. Our approach enables the easy generation of complex thioglycoside atropoisomers, thus paving the way to new products of potential biological interest.

langue originale	Anglais
Pages (de - à)	10355-10358
Nombre de pages	4
journal	Chemical Communications
Volume	57
Numéro de publication	80
Les DOIs	https://doi.org/10.1039/d1cc03971g
état	Publié - 14 oct. 2021
Modification externe	Oui

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10.1039/d1cc03971g

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title = "Synthesis of axially chiral biaryl thioglycosides through thiosugar-directed Pd-catalyzed asymmetric C-H activation",

abstract = "Herein we report for the first time that the thiosugar moiety can be used both as a directing group enabling the regioselective activation of a C-H bond of biaryl scaffolds and as a chiral source inducing axial chirality. Our approach enables the easy generation of complex thioglycoside atropoisomers, thus paving the way to new products of potential biological interest.",

author = "Maha Fatthalla and Nicolas Grimblat and Etienne Brachet and Mouad Alami and Vincent Gandon and \{Le Bideau\}, Franck and Samir Messaoudi",

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T1 - Synthesis of axially chiral biaryl thioglycosides through thiosugar-directed Pd-catalyzed asymmetric C-H activation

AU - Fatthalla, Maha

AU - Grimblat, Nicolas

AU - Brachet, Etienne

AU - Alami, Mouad

AU - Gandon, Vincent

AU - Le Bideau, Franck

AU - Messaoudi, Samir

PY - 2021/10/14

Y1 - 2021/10/14

N2 - Herein we report for the first time that the thiosugar moiety can be used both as a directing group enabling the regioselective activation of a C-H bond of biaryl scaffolds and as a chiral source inducing axial chirality. Our approach enables the easy generation of complex thioglycoside atropoisomers, thus paving the way to new products of potential biological interest.

AB - Herein we report for the first time that the thiosugar moiety can be used both as a directing group enabling the regioselective activation of a C-H bond of biaryl scaffolds and as a chiral source inducing axial chirality. Our approach enables the easy generation of complex thioglycoside atropoisomers, thus paving the way to new products of potential biological interest.

U2 - 10.1039/d1cc03971g

DO - 10.1039/d1cc03971g

M3 - Article

C2 - 34533145

AN - SCOPUS:85116632584

SN - 1359-7345

VL - 57

SP - 10355

EP - 10358

JO - Chemical Communications

JF - Chemical Communications

IS - 80

ER -

Synthesis of axially chiral biaryl thioglycosides through thiosugar-directed Pd-catalyzed asymmetric C-H activation

Résumé

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