A Homodinuclear Mn(III)2−Schiff Base Complex for Catalytic Asymmetric 1,4-Additions of Oxindoles to Nitroalkenes
Catalytic asymmetric 1,4-additions of 3-substituted oxindoles to β-aryl, β-heteroaryl, and β-alkenyl nitroalkenes are described. A new homodinuclear Mn2(OAc)2−Schiff base 1 complex was required to realize high diastereo- and enantioselectivity. Mn2(OAc)2−1 (1−5 mol %) promoted the 1,4-additions in 9...
Gespeichert in:
Veröffentlicht in: | Journal of the American Chemical Society 2009-07, Vol.131 (26), p.9168-9169 |
---|---|
Hauptverfasser: | , , , , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
Zusammenfassung: | Catalytic asymmetric 1,4-additions of 3-substituted oxindoles to β-aryl, β-heteroaryl, and β-alkenyl nitroalkenes are described. A new homodinuclear Mn2(OAc)2−Schiff base 1 complex was required to realize high diastereo- and enantioselectivity. Mn2(OAc)2−1 (1−5 mol %) promoted the 1,4-additions in 99−83% yield, 96−85% ee, and >30:1−5:1 dr at room temperature, providing useful chiral building blocks for the synthesis of β-aminooxindoles with vicinal quaternary/tertiary carbon stereocenters. |
---|---|
ISSN: | 0002-7863 1520-5126 |
DOI: | 10.1021/ja903566u |