Asymmetric Ion Pair Catalysis of 6 pi Electrocyclizations: Broensted Acid Catalyzed Enantioselective Synthesis of Optically Active 1,4-Dihydropyridazines

Asymmetric Ion Pair Catalysis of 6 pi Electrocyclizations: Broensted Acid Catalyzed Enantioselective Synthesis of Optically Active 1,4-Dihydropyridazines

Electric slide: Described is a general, operationally simple, highly enantioselective Broensted acid catalyzed condensation/6 pi -electrocyclization reaction between hydrazones and [alpha],[beta]-unsaturated aldehydes that yields valuable 1,4-dihydropyridazines. The reaction exhibits high tolerance...

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Veröffentlicht in:Angewandte Chemie International Edition 2013-07, Vol.52 (31), p.8008-8011
Hauptverfasser: Das, Arindam, Volla, Chandra MR, Atodiresei, Iuliana, Bettray, Wolfgang, Rueping, Magnus
Format: Artikel
Sprache:eng
Schlagworte:
Asymmetry
Catalysis
Functional groups
Hydrazones
Ion pairs
Optical activity
Synthesis
Tolerances
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Beschreibung
Zusammenfassung:Electric slide: Described is a general, operationally simple, highly enantioselective Broensted acid catalyzed condensation/6 pi -electrocyclization reaction between hydrazones and [alpha],[beta]-unsaturated aldehydes that yields valuable 1,4-dihydropyridazines. The reaction exhibits high tolerance towards functional groups and affords products with up to 98% ee.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201301638