Download PDF
Synlett 1999; 1999(4): 441-443
DOI: 10.1055/s-1999-2641
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Tandem Cyclisations of Amidyl Radicals Derived from O-Acyl Hydroxamic Acid Derivatives

Andrew J. Clark* , Robert P. Filik, Joanne L. Paecock, Gerard H. Thomas
  • *Department of Chemistry, University of Warwick, Coventry, CV4 7AL, UK; Fax +44(12 03)52 41 12; E-mail: msrir@csv.warwick.ac.uk
Further Information

Publication History

Publication Date:
31 December 1999 (online)

  PDF Download  Permissions and Reprints All articles of this category

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

      >