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

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

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

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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:
asymmetric catalysis
Brønsted acid
chiral anions
ion pairs
organocatalysis
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Zusammenfassung:Caught in the act: A new concept for asymmetric Brønsted acid catalysis is presented. Compounds containing an acidic functionality in addition to an anion recognition site act as powerful conjugate‐base‐stabilized Brønsted 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