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|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|
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