Diastereoselective Ritter reactions of chiral cyclic N-acyliminium ions: synthesis of pyrido- and pyrrolo[2,3-d]oxazoles and 4-Hydroxy-5-N-acylaminopyrrolidines and 5-hydroxy-6-N-acylaminopiperidines.
Pyrido- and pyrrolo[2,3-d]oxazoles can be conveniently prepared in high yield from the Ritter reaction of nitriles and in situ generated chiral cyclic N-acyliminium ions. cis-4-Hydroxy-5-acylaminopyrrolidines and cis-5-hydroxy-6-acylaminopiperidines can be readily obtained by acid hydrolysis of these bicyclic heterocyclic compounds, respectively.
Morgan
Ian R
IR
School of Chemistry, University of Wollongong, Wollongong, New South Wales 2522, Australia.
Yazici
Arife
A
Pyne
Stephen G
SG
Skelton
Brian W
BW
D007097:Imines / Q000737:chemistry*; D008968:Molecular Conformation; D009570:Nitriles / Q000737:chemistry; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D007097:Imines; D009570:Nitriles; D010080:Oxazoles; D010880:Piperidines; D011759:Pyrrolidines