Alkynyliodonium salt mediated alkynylation of azlactones: fast access to C(α)-tetrasubstituted α-amino acid derivatives

Alkynyliodonium salt mediated alkynylation of azlactones: fast access to C(α)-tetrasubstituted α-amino acid derivatives

An efficient electrophilic alkynylation of azlactones (oxazol-5(4H)-ones) is developed using alkynyl(phenyl)iodonium salts as the electrophilic alkyne source. After remarkably short reaction times, the desired alkyne functionalized azlactones are obtained in 60-97% yield and can be transformed easil...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2014-03, Vol.16 (5), p.1326-1329
Hauptverfasser: Finkbeiner, Peter, Weckenmann, Nicole M, Nachtsheim, Boris J
Format: Artikel
Sprache:eng
Schlagworte:
Alkynes - chemistry
Amino Acids - chemical synthesis
Amino Acids - chemistry
Catalysis
Lactones - chemistry
Molecular Structure
Salts
Stereoisomerism
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:An efficient electrophilic alkynylation of azlactones (oxazol-5(4H)-ones) is developed using alkynyl(phenyl)iodonium salts as the electrophilic alkyne source. After remarkably short reaction times, the desired alkyne functionalized azlactones are obtained in 60-97% yield and can be transformed easily into a variety of quaternary α-amino acid derivatives.
ISSN:1523-7052
DOI:10.1021/ol500053c