Epoxidation of electron deficient alkenes using tert-butyl hydroperoxide and 1,5,7-triazabicyclo[4.4.0]dec-5-ene and its derivatives

Authors
Genski, T Macdonald, G Wei, XD Lewis, N Taylor, RJK
Citation
T. Genski et al., Epoxidation of electron deficient alkenes using tert-butyl hydroperoxide and 1,5,7-triazabicyclo[4.4.0]dec-5-ene and its derivatives, SYNLETT, (6), 1999, pp. 795-797
Citations number
17
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
6
Year of publication
1999
Pages
795 - 797
Database
ISI
SICI code
0936-5214(199906):6<795:EOEDAU>2.0.ZU;2-Y
Abstract
The title cyclic guanidine (4a) is an efficient promoter of enone epoxidati on by tert-butyl hydroperoxide. Optimisation studies are reported and the p rocedure applied to cyclic and acyclic ketones, quinones and naphthoquinone s. N-Substituted guanidine (4c) proved best for the epoxidation of 2-amidob enzoquinones. Preliminary asymmetric epoxidation studies are also discussed .