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Synlett 2000; 2000(5): 0704-0706
DOI: 10.1055/s-2000-6619
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The Enantioselective Epoxidation of Quinones Using Sugar Hydroperoxides

Catherine L. Dwyer* , Christopher D.  Gill, Osamu Ichihara, Richard J. K. Taylor
  • *Department of Chemistry, University of York, Heslington, York YO10 5DD, UK; Fax + 44(0)1904-43 45 23; E-mail: rjkt1@york.ac.uk
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Publication Date:
31 December 2000 (online)

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Sugar-derived hydroperoxides have been employed for DBU-promoted enantioselective epoxidation reactions. Optimisation studies are reported using 2-(5-cyclohexylpentadienamido)-1,4-benzoquinone (maximum ee = 67%); the resulting epoxide is an important synthetic precursor for the antibiotic (-)-Alisamycin. The procedure has also been applied to a range of 2-substituted naphthoquinones (maximum ee = 82%).

epoxidation - sugar hydroperoxides - quinones