A general approach to aza-heterocycles by means of domino sequences driven by hydroformylation.
The development of hydroformylative domino reactions of easily accessible vinyl acetamides is described. Extremely regioselective hydroformylation of terminal double bounds provides a transient N-acyliminium that can be trapped by various nucleophiles to give several aza-heterocylic scaffolds in a diastereoselective manner.
Airiau
Etienne
E
Faculté de Pharmacie, Université Louis Pasteur de Strasbourg, Laboratoire de Pharmacochimie de la Communication Cellulaire UMR 7175/LC1, 74, route du Rhin, BP 60024, 67401 Illkirch, France.
Spangenberg
Thomas
T
Girard
Nicolas
N
Schoenfelder
Angèle
A
Salvadori
Jessica
J
Taddei
Maurizio
M
Mann
André
A
D000081:Acetamides / Q000737:chemistry; D001372:Aza Compounds / Q000138:chemical synthesis*; D003500:Cyclization; D005561:Formates; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D007212:Indolizines / Q000138:chemical synthesis; D013237:Stereoisomerism
D000081:Acetamides; D001372:Aza Compounds; D005561:Formates; D006571:Heterocyclic Compounds; D007202:Indicators and Reagents; D007212:Indolizines; C030544:formic acid