Diastereoselective preparation of azetidines and pyrrolidines |
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Authors: | Feula Antonio Male Louise Fossey John S |
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Institution: | School of Chemistry, University of Birmingham, Edgbaston, Birmingham, West Midlands, B15 2TT, United Kingdom. |
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Abstract: | 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. |
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