Enantioselective Au-Catalyzed Synthesis of Thia[5]- and Thia[6]helicenes and Their Transformation into Bowl-shaped Pleiadenes.
Au-catalysis
alkyne hydroarylation
asymmetric catalysis
bowl-shaped molecules
thiahelicenes
Journal
Advanced materials (Deerfield Beach, Fla.)
ISSN: 1521-4095
Titre abrégé: Adv Mater
Pays: Germany
ID NLM: 9885358
Informations de publication
Date de publication:
Apr 2023
Apr 2023
Historique:
revised:
17
01
2023
received:
02
12
2022
medline:
8
2
2023
pubmed:
8
2
2023
entrez:
7
2
2023
Statut:
ppublish
Résumé
A series of helically shaped benzo[b]chryseno[4,3-d]thiophenes, naphtho[1,2-b]phenanthro[4,3-d]thiophenes, and chryseno[3,4-b]naphtho[1,2-d]thiophenes is synthesized via a highly enantioselective Au-catalyzed intramolecular alkyne hydroarylation reaction. The inversion barriers of the structures obtained are determined both theoretically and experimentally, and their chiroptical properties are reported. Preliminary studies on the post-synthetic functionalization of these thiahelicenes and their transformation into azahelicenes are also presented. In addition, a straightforward one-step protocol is developed, which wraps the initially obtained chryseno[3,4-b]naphtho[1,2-d]thiophenes into bowl-shaped pleiadene derivatives without erosion of the enantiopurity. The number of structurally related products that are obtained with high enantioselectivity enables the establishment of comprehensive correlations between the structure and conformational stability or (chir)optical properties.
Identifiants
pubmed: 36747350
doi: 10.1002/adma.202211279
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e2211279Subventions
Organisme : Deutsche Forschungsgemeinschaft
ID : INST 186/1352-1
Organisme : Deutsche Forschungsgemeinschaft
ID : INST 186/1237-1
Organisme : China Scholarship Council
Informations de copyright
© 2023 The Authors. Advanced Materials published by Wiley-VCH GmbH.
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