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Synlett 1999; 1999(4): 441-443
DOI: 10.1055/s-1999-2641
DOI: 10.1055/s-1999-2641
letter
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Tandem Cyclisations of Amidyl Radicals Derived from O-Acyl Hydroxamic Acid Derivatives
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Publikationsverlauf
Publikationsdatum:
31. Dezember 1999 (online)
![](https://www.thieme-connect.de/media/synlett/199904/lookinside/thumbnails/10.1055-s-1999-2641-1.jpg)
Amidyl radicals generated from tributylstannane mediated homolysis of O-acyl hydroxamic acid derivatives 5a-b undergo tandem cyclisations to give pyrrolizidinones 6a-c and indolizidinones 7a-b respectively while 5c-d undergo monocyclisation to give β-lactam 10a and γ-lactam 11a respectively. On the other hand the reaction of 5d-f with Cu(OTf)2/DBN furnishes mixtures of reduction 10b, monocyclisation 10a and tandem cyclisation 9 products with the ratio dependant upon the nature of the O-acyl group and the solvent and concentration employed.
amidyl radicals - cyclisation - copper complexes - hydroxamic acid derivatives