Synthesis of Enantioenriched Indolines by a Conjugate Addition/Asymmetric Protonation/Aza-Prins Cascade Reaction

A conjugate addition/asymmetric protonation/aza‐Prins cascade reaction has been developed for the enantioselective synthesis of fused polycyclic indolines. A catalyst system generated from ZrCl4 and 3,3′‐dibromo‐BINOL enables the synthesis of a range of polycyclic indolines in good yields and with h...

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Bibliographic Details
Published in:Angewandte Chemie 2016-03, Vol.128 (10), p.3459-3463
Main Authors: Daniels, Blake E., Ni, Jane, Reisman, Sarah E.
Format: Article
Language:English
Subjects:
Acids
Asymmetry
Cascade chemical reactions
Catalysts
Chemical synthesis
Chemistry
Conjugates
Cyclisierungen
Dibromophenol
Enantiomers
Enantioselektivität
Heterocyclen
Heterocyclic aromatic compounds
Heterocyclic compounds
Lewis-Säuren
Protonation
Synthesis (chemistry)
Transformations
Zirconium
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Summary:A conjugate addition/asymmetric protonation/aza‐Prins cascade reaction has been developed for the enantioselective synthesis of fused polycyclic indolines. A catalyst system generated from ZrCl4 and 3,3′‐dibromo‐BINOL enables the synthesis of a range of polycyclic indolines in good yields and with high enantioselectivity. A key finding is the use of TMSCl and 2,6‐dibromophenol as a stoichiometric source of HCl to facilitate catalyst turnover. This transformation is the first in which a ZrCl4⋅BINOL complex serves as a chiral Lewis‐acid‐assisted Brønsted acid. Zr Hilfe! Bei der Titelreaktion unter Brønsted‐Säure‐Katalyse wirkt eine Zirconium‐Lewis‐Säure unterstützend. Polycyclische Indoline werden hoch enantioselektiv und in guten Ausbeuten synthetisiert.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201510972