Selective Ring-Opening Amination of Isochromans and Tetrahydroisoquinolines.
Amination
C−C Bond Cleavage
Molecular Editing
Rearrangement Reaction
Transition-Metal Free
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
08 Mar 2024
08 Mar 2024
Historique:
received:
19
01
2023
pubmed:
9
3
2024
medline:
9
3
2024
entrez:
9
3
2024
Statut:
aheadofprint
Résumé
The molecular structure-editing through selective C-C bond cleavage allows for the precise modification of molecular structures and opens up new possibilities in chemical synthesis. By strategically cleaving C-C bonds and editing the molecular structure, more efficient and versatile pathways for the synthesis of complex compounds could be designed, which brings significant implications for drug development and materials science. o-Aminophenethyl alcohols and amines are the essential key motifs in bioactive and functional material molecules. The traditional synthesis of these compounds usually requires multiple steps which could generate inseparable isomers and induce low efficiencies. By leveraging a molecular editing strategy, we herein reported a selective ring-opening amination of isochromans and tetrahydroisoquinolines for the efficient synthesis of o-aminophenethyl alcohols and amines. This innovative chemistry allows for the precise cleavage of C-C bonds under mild transition metal-free conditions. Notably, further synthetic application demonstrated that our method could provide an efficient approach to essential components of diverse bioactive molecules.
Identifiants
pubmed: 38459760
doi: 10.1002/anie.202401318
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202401318Subventions
Organisme : National Key R&D Program of China
ID : 2021YFA1501700
Organisme : National Natural Science Foundation of China
ID : 22371203
Organisme : National Natural Science Foundation of China
ID : 22131002
Organisme : National Natural Science Foundation of China
ID : 22071005
Organisme : National Natural Science Foundation of China
ID : 22161142019
Organisme : Beijing Nova Program
ID : Z201100006820099
Informations de copyright
© 2024 Wiley-VCH GmbH.
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