Thermal rearrangement of 2-bromooxazolines to 2-bromoisocyanates.
Fiche publication
Date publication
janvier 2008
Auteurs
Membres identifiés du Cancéropôle Est :
Dr BELLEMIN-LAPONNAZ Stéphane
Tous les auteurs :
Foltz C, Bellemin-Laponnaz S, Enders M, Wadepohl H, Gade LH
Lien Pubmed
Résumé
A unprecedented thermally induced rearrangement of 2-bromo-4-substituted oxazolines into 2-bromoisocyanates with high selectivity has been observed. Isolated yields of 85-90% were obtained with 2-bromo-4-phenyloxazoline, 2-bromo-4-isopropyloxazoline, or 2-bromo-4,4dimethyloxazoline. In addition, chiral aziridinecarboxamdes or 2-aminooxazolines could be selectively obtained from the corresponding 2-bromo isocyanate depending on reaction conditions.
Référence
Org Lett. 2008 Jan 17;10(2):305-8