Please use this identifier to cite or link to this item:
|Title:||Base- and Co(II)-catalyzed ring-opening reactions of perhydrooxireno[2,3-d][1,2]dioxines: An efficient route to 4-hydroxy-2,3-epoxy-ketones|
|Citation:||Greatrex, B.W., Jenkins, N.F., Taylor, D.K., Tiekink, E.R.T. (2003-06-27). Base- and Co(II)-catalyzed ring-opening reactions of perhydrooxireno[2,3-d][1,2]dioxines: An efficient route to 4-hydroxy-2,3-epoxy-ketones. Journal of Organic Chemistry 68 (13) : 5205-5210. ScholarBank@NUS Repository. https://doi.org/10.1021/jo0300845|
|Abstract:||A series of 3,4,6-substituted 3,6-dihydro-1,2-dioxines were epoxidized with m-chloroperbenzoic acid to furnish perhydrooxireno[2,3-d][1,2]dioxines (epoxy-1,2-dioxines) in yields ranging from 51% to 93% with de's from 26% to 100%. Unsymmetrical epoxy-1,2-dioxines were ring-opened using triethylamine to yield 4-hydroxy-2,3-epoxy-ketones quantitatively, and meso-epoxy-1,2-dioxines were ring-opened using Co(II) salen complexes to afford 4-hydroxy-2,3-epoxy-ketones in 77-98% yield. The first reported examples of the catalytic asymmetric ring-opening of meso-epoxy-1,2-dioxines using a range of chiral Co(II) salen and β-ketoiminato complexes to afford highly enantio-enriched 4-hydroxy-2,3-epoxy-ketones are also presented.|
|Source Title:||Journal of Organic Chemistry|
|Appears in Collections:||Staff Publications|
Show full item record
Files in This Item:
There are no files associated with this item.
checked on Sep 21, 2018
WEB OF SCIENCETM
checked on Sep 11, 2018
checked on Sep 14, 2018
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.