Please use this identifier to cite or link to this item: https://doi.org/10.1021/jo0300845
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
Authors: Greatrex, B.W.
Jenkins, N.F.
Taylor, D.K.
Tiekink, E.R.T. 
Issue Date: 27-Jun-2003
Source: 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
URI: http://scholarbank.nus.edu.sg/handle/10635/75644
ISSN: 00223263
DOI: 10.1021/jo0300845
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