Aminocatalytic [8+2] Cycloaddition Reactions toward Chiral Cyclazines.
asymmetric synthesis
cycloaddition
fused-ring systems
nitrogen heterocycles
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:
16 Aug 2021
16 Aug 2021
Historique:
received:
10
05
2021
pubmed:
9
6
2021
medline:
9
6
2021
entrez:
8
6
2021
Statut:
ppublish
Résumé
An efficient and exceptionally stereoselective synthesis of chiral cycl[3.2.2]azines has been realized by means of the rational design and utilization of novel (E)-3-benzylidene-3H-pyrrolizines in iminium-ion-catalyzed [8+2] cycloaddition reactions. The presented protocol allows for the incorporation of diverse enals, including cinnamaldehydes, enolizable aldehydes, and substrates of extended conjugation. The obtained products contain both an electron-rich alkenyl pyrrole moiety and an electron-deficient carbaldehyde substituent, and both moieties can undergo selective transformations with retention of the stereochemical information established in the [8+2] cycloaddition.
Identifiants
pubmed: 34101936
doi: 10.1002/anie.202106287
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
18527-18531Subventions
Organisme : Villum Fonden
ID : 25867
Organisme : Carlsbergfondet
Informations de copyright
© 2021 Wiley-VCH GmbH.
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