Asymmetric oxidation of enol phosphates to α-hydroxy ketones using Sharpless reagents and a fructose derived dioxirane

The asymmetric oxidation of a variety of differently substituted, acyclic and cyclic enol phosphates using the Sharpless AD-reagents AD-mix-α and AD-mix-β, and a fructose derived chiral ketone as a catalyst, afforded the corresponding α-hydroxy ketones in high enantioselectivity and good yield. The...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2012-11, Vol.23 (20-21), p.1480-1489
Main Authors: Krawczyk, Ewa, Mielniczak, Grażyna, Owsianik, Krzysztof, Łuczak, Jerzy
Format: Article
Language:English
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Summary:The asymmetric oxidation of a variety of differently substituted, acyclic and cyclic enol phosphates using the Sharpless AD-reagents AD-mix-α and AD-mix-β, and a fructose derived chiral ketone as a catalyst, afforded the corresponding α-hydroxy ketones in high enantioselectivity and good yield. The influence of steric and electronic factors of the substrates on the facial stereoselectivity in the reported oxidations was studied.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2012.09.012