Asymmetric epoxidation by chiral ketones derived from carbocyclic analogues of fructose.
A number of carbocyclic analogues of the fructose-derived ketone 1 have been prepared and investigated for asymmetric epoxidation. The studies show that 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.
Wang
Z X
ZX
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
Miller
S M
SM
Anderson
O P
OP
Shi
Y
Y
D002236:Carbohydrate Conformation; D004852:Epoxy Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D005632:Fructose / Q000031:analogs & derivatives* / Q000737:chemistry*; D007202:Indicators and Reagents; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D004852:Epoxy Compounds; D007202:Indicators and Reagents; D007659:Ketones; D005632:Fructose