Asymmetric epoxidation by chiral ketones derived from carbocyclic analogues of fructose

Authors
Wang, ZX Miller, SM Anderson, OP Shi, Y
Citation
Zx. Wang et al., Asymmetric epoxidation by chiral ketones derived from carbocyclic analogues of fructose, J ORG CHEM, 66(2), 2001, pp. 521-530
Citations number
62
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
66
Issue
2
Year of publication
2001
Pages
521 - 530
Database
ISI
SICI code
0022-3263(20010126)66:2<521:AEBCKD>2.0.ZU;2-N
Abstract
A number of carbocyclic analogues of the fructose-derived ketone 1 have bee n prepared and investigated for asymmetric epoxidation. The studies show th at the oxygen atom of the pyranose ring of 1 has an impact on the catalyst' s activity and selectivity. Conformational, electronic, and steric effects are discussed.