Diastereoselective 1,3-Dipolar Cycloaddition of Nitrones to Donor–Acceptor Cyclopropanes Catalyzed by a Calcium(II) Complex

Calcium triflate has been identified as an efficient catalyst for the cycloaddition of nitrones to donor–acceptor cyclopropanes. The reaction proceeds with good to excellent yields of the corresponding tetrahydro-1,2-oxazines with high levels of diastereoselectivity. The generality of the reaction a...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2015-02, Vol.80 (3), p.1979-1984
Hauptverfasser: Braun, Caroline M, Congdon, Elizabeth A, Nolin, Kristine A
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Calcium triflate has been identified as an efficient catalyst for the cycloaddition of nitrones to donor–acceptor cyclopropanes. The reaction proceeds with good to excellent yields of the corresponding tetrahydro-1,2-oxazines with high levels of diastereoselectivity. The generality of the reaction allowed for the synthesis of tetrahydro-1,2-oxazines bearing alkyl, aryl, and heteroaromatic substitution.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo502686t