Highly Enantioselective Pictet-Spengler Reactions with α-Ketoamide-Derived Ketimines: Access to an Unusual Class of Quaternary α-Amino Amides

Highly Enantioselective Pictet-Spengler Reactions with α-Ketoamide-Derived Ketimines: Access to an Unusual Class of Quaternary α-Amino Amides

"Quat's" the story? N-Aryl amides are effective directing/activating groups for chlorosilane Lewis acids. This aspect has been exploited for the development of the first simple and general method for the highly enantioselective Pictet-Spengler reaction of ketimines derived from α-keto...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2009-01, Vol.48 (13), p.2403-2406
Hauptverfasser: Bou-Hamdan, Farhan R, Leighton, James L
Format: Artikel
Sprache:eng
Schlagworte:
Amides - chemistry
Amino Acids - chemistry
asymmetric synthesis
Catalysis
heterocycles
Heterocyclic Compounds - chemical synthesis
Heterocyclic Compounds - chemistry
ketimines
Lewis acids
Pictet–Spengler reaction
Silanes - chemistry
Stereoisomerism
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Beschreibung
Zusammenfassung:"Quat's" the story? N-Aryl amides are effective directing/activating groups for chlorosilane Lewis acids. This aspect has been exploited for the development of the first simple and general method for the highly enantioselective Pictet-Spengler reaction of ketimines derived from α-ketoamides leading to quaternary α-amino acid derivatives (see scheme).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200806110