Organocatalyzed Regioselective Synthesis of 1,5-Disubstituted 1,2,3-Triazolyl Glycoconjugates.
carbohydrate
click chemistry
organocatalysis
regioselectivity
triazole
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
02 Oct 2023
02 Oct 2023
Historique:
received:
01
06
2023
medline:
11
7
2023
pubmed:
11
7
2023
entrez:
11
7
2023
Statut:
ppublish
Résumé
A novel organocatalyzed [3+2] cycloaddition reaction of nitroolefins with glycosyl azides as well as organic azides has been developed for successful construction of 1,5-disubstituted triazolyl glycoconjugates. This metal-free and acid-free, regioselective synthetic protocol proceeds in the presence of only Schreiner thiourea organocatalysts, which enable the required activation of nitroolefins through double hydrogen bonding. The straightforward, operationally simple, and regioselectivity of this methodology, complementing to the classical RuAAC catalyzed synthesis of 1,5-disubstituted 1,2,3-triazoles. In the presence of catalytic amount of Schreiner thiourea organocatalyst, organic azides react with a broad array of nitroolefins producing a series of diverse 1,5-disubstituted 1,2,3- triazoles in good yields with excellent regioselectivity.
Identifiants
pubmed: 37432103
doi: 10.1002/chem.202301749
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202301749Subventions
Organisme : Science and Engineering Research Board, India
ID : Grant No.: CRG/2021/002776
Informations de copyright
© 2023 Wiley-VCH GmbH.
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