The enantioselective epoxidation of quinones using sugar hydroperoxides

Authors
Dwyer, CL Gill, CD Ichihara, O Taylor, RJK
Citation
Cl. Dwyer et al., The enantioselective epoxidation of quinones using sugar hydroperoxides, SYNLETT, (5), 2000, pp. 704-706
Citations number
24
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
5
Year of publication
2000
Pages
704 - 706
Database
ISI
SICI code
0936-5214(200005):5<704:TEEOQU>2.0.ZU;2-K
Abstract
Sugar-derived hydroperoxides have been employed for DBU-promoted enantiosel ective 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 (-)-Alisamy cin. The procedure has also been applied to a range of 2-substituted naphth oquinones (maximum ee = 82%).