Tetrahedron: Asymmetry

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

E Krawczyk, G Mielniczak, K Owsianik, J Łuczak

Index: Krawczyk, Ewa; Mielniczak, Grazyna; Owsianik, Krzysztof; Luczak, Jerzy Tetrahedron Asymmetry, 2012 , vol. 23, # 20-21 p. 1480 - 1489

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Citation Number: 8

Abstract

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.