Ceric ammonium nitrate promoted free radical cyclization reactions leading to β-lactams

The reaction of enamides with CAN in methanol affords variously functionalized β-lactams through a 4- exo- trig cyclization of α-carbamoylalkyl radicals; in most cases products with trans stereochemistry can be obtained. A 4- exo- trig radical cyclization of N-alkenyl amides promoted by Ce(IV) affor...

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Bibliographic Details
Published in:Tetrahedron letters 1997-03, Vol.38 (10), p.1829-1832
Main Authors: D'Annibale, Andrea, Pesce, Antonella, Resta, Stefano, Trogolo, Corrado
Format: Article
Language:English
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Summary:The reaction of enamides with CAN in methanol affords variously functionalized β-lactams through a 4- exo- trig cyclization of α-carbamoylalkyl radicals; in most cases products with trans stereochemistry can be obtained. A 4- exo- trig radical cyclization of N-alkenyl amides promoted by Ce(IV) affords azetidin-2-ones.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(97)00162-7