Conjugate-Base-Stabilized Broensted Acids as Asymmetric Catalysts: Enantioselective Povarov Reactions with Secondary Aromatic Amines

Conjugate-Base-Stabilized Broensted Acids as Asymmetric Catalysts: Enantioselective Povarov Reactions with Secondary Aromatic Amines

Caught in the act: A new concept for asymmetric Broensted acid catalysis is presented. Compounds containing an acidic functionality in addition to an anion recognition site act as powerful conjugate-base-stabilized Broensted acid catalysts. This strategy was applied to the first catalytic enantiosel...

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Veröffentlicht in:Angewandte Chemie International Edition 2013-12, Vol.52 (52), p.14084-14088
Hauptverfasser: Min, Chang, Mittal, Nisha, Sun, Diana X, Seidel, Daniel
Format: Artikel
Sprache:eng
Schlagworte:
Amines
Anions
Asymmetry
Catalysis
Catalysts
Recognition
Sieves
Strategy
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Zusammenfassung:Caught in the act: A new concept for asymmetric Broensted acid catalysis is presented. Compounds containing an acidic functionality in addition to an anion recognition site act as powerful conjugate-base-stabilized Broensted acid catalysts. This strategy was applied to the first catalytic enantioselective three-component Povarov reaction of indoline and other secondary aromatic amines (see scheme; M.S.=molecular sieves).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201308196