Brønsted Acid-Catalyzed Desymmetrization of meso-Aziridines

The enantioselective ring-opening of meso-aziridines with azide nucleophiles proceeded in the presence of a catalytic amount of a chiral phosphoric acid catalyst. The reaction affords the formation of the products in excellent yield and enantioselectivity. Preliminary mechanistic studies indicate th...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of the American Chemical Society 2007-10, Vol.129 (40), p.12084-12085
Hauptverfasser: Rowland, Emily B, Rowland, Gerald B, Rivera-Otero, Edwin, Antilla, Jon C
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:The enantioselective ring-opening of meso-aziridines with azide nucleophiles proceeded in the presence of a catalytic amount of a chiral phosphoric acid catalyst. The reaction affords the formation of the products in excellent yield and enantioselectivity. Preliminary mechanistic studies indicate that the active catalytic species is a chiral silane that is generated in situ.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja0751779