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Synlett 1999; 1999(6): 795-797
DOI: 10.1055/s-1999-2721
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Epoxidation of Electron Deficient Alkenes Using tert-Butyl Hydroperoxide and 1,5,7-Triazabicyclo[4.4.0]dec-5-ene and its Derivatives

Thorsten Genski* , Gregor Macdonald, Xudong Wei, Norman Lewis, Richard J. K. Taylor
  • *Department of Chemistry, University of York, Heslington, York YO10 5DD, UK; Fax +44 (0) 19 04-43 45 23; E-mail: rjkt1@york.ac.uk
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Publication Date:
31 December 1999 (online)

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The title cyclic guanidine (4a) is an efficient promoter of enone epoxidation by tert-butyl hydroperoxide. Optimisation studies are reported and the procedure applied to cyclic and acyclic ketones, quinones and naphthoquinones. N-Substituted guanidine (4c) proved best for the epoxidation of 2-amidobenzoquinones. Preliminary asymmetric epoxidation studies are also discussed.

epoxidation - alkenes - guanidine