Diastereoselective preparation of azetidines and pyrrolidines.
Iodine-mediated cyclization of homoallyl amines at room temperature delivered cis-2,4-azetidine through a 4-exo trig cyclization. Isomerization of iodo-azetidines to cis-pyrrolidines could be achieved by heating, with complete stereocontrol. The relative stereochemistry of the iodo-azetidines and pyrrolidines was confirmed by NMR spectroscopy and X-ray crystallography. Further functionalization was achieved through nucleophilic displacement of iodine to deliver substituted azetidines and pyrrolidines. 1,2,3-Triazole-appended azetidines and pyrrolidines were also prepared.
Feula
Antonio
A
School of Chemistry, University of Birmingham, Edgbaston, Birmingham, West Midlands, B15 2TT, United Kingdom.
Male
Louise
L
Fossey
John S
JS
D001384:Azetidines / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D003500:Cyclization; D008958:Models, Molecular; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D001384:Azetidines; D011759:Pyrrolidines