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https://hdl.handle.net/2440/18009
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Type: | Journal article |
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 |
Author: | Greatrex, B. Jenkins, N. Taylor, D. Tiekink, E. |
Citation: | Journal of Organic Chemistry, 2003; 68(13):5205-5210 |
Publisher: | Amer Chemical Soc |
Issue Date: | 2003 |
ISSN: | 0022-3263 1520-6904 |
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. |
DOI: | 10.1021/jo0300845 |
Published version: | http://dx.doi.org/10.1021/jo0300845 |
Appears in Collections: | Aurora harvest 2 Chemistry publications |
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