Diastereoselective epoxidation of cyclohexene derivatives by dioxiranes generated in situ. Importance of steric and field effects

Authors
Yang, D Jiao, GS Yip, YC Wong, MK
Citation
D. Yang et al., Diastereoselective epoxidation of cyclohexene derivatives by dioxiranes generated in situ. Importance of steric and field effects, J ORG CHEM, 64(5), 1999, pp. 1635-1639
Citations number
75
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
64
Issue
5
Year of publication
1999
Pages
1635 - 1639
Database
ISI
SICI code
0022-3263(19990305)64:5<1635:DEOCDB>2.0.ZU;2-H
Abstract
In this paper, diastereoselective epoxidation of substituted cyclohexenes ( substrates 1-7) by dioxiranes generated in situ from ketones and Oxone was systematically investigated. The results revealed that the diastereoselecti vity was determined by the steric and held effects of both dioxiranes and s ubstrates, and high diastereoselectivity can be achieved by tuning the keto ne structure. Among the ketones tested, 12 and 19 gave the best diastereose lectivities.