Fine-Tuning Substrate-Catalyst Halogen-Halogen Interactions for Boosting Enantioselectivity in Halogen-Bonding Catalysis.
Anion-Binding
Asymmetric Catalysis
Halogen-Bonding
Noncovalent Interactions
Organocatalysis
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:
28 Aug 2023
28 Aug 2023
Historique:
received:
04
04
2023
medline:
25
5
2023
pubmed:
25
5
2023
entrez:
25
5
2023
Statut:
ppublish
Résumé
A new approach towards highly enantioselective halogen-bonding catalysis has been developed. To circumvent the intrinsic issues of the nature of the halogen-bond (XB) and the resultant unresolved limitations in asymmetric catalysis, fine-tuned halogen-halogen interactions between the substrate and XB-donor were designed to preorganize the substrate in the catalyst's cavity and boost enantiocontrol. The present strategy exploits both the electron cloud (Lewis base site) and the sigma (σ)-hole site of the halogen substituent of the substrates to form a tight catalyst-substrate-counteranion chiral complex, thus enabling a controlled induction of high levels of chirality transfer. Remarkable enantioselectivities of up to 95 : 5 e.r. (90 % ee) have been achieved in a model dearomatization reaction of halogen-substituted (iso)quinolines with tetrakis-iodotriazole multidentate anion-binding catalysts.
Identifiants
pubmed: 37228095
doi: 10.1002/anie.202304781
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202304781Subventions
Organisme : H2020 European Research Council
ID : ERC-CG 724695
Organisme : Deutsche Forschungsgemeinschaft
Organisme : H2020 Marie Skłodowska-Curie Actions
ID : 847413
Informations de copyright
© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
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