Ketone-catalyzed asymmetric epoxidation

Chiral ketone-catalyzed asymmetric epoxidation has received intensive interest since the first reported by Curci et al. in 1984. The reaction is performed with oxone (potassium peroxomonosulfate) as the primary oxidant which generates the chiral dioxirane catalytic species in situ, which in turn, transfers the oxygen... 

Frohn, M. Shi, Y. Chiral Ketone-Catalyzed Asymmetric Epoxidation of Olefins, Synthesis 2000, 1979-2000. 

Yang D. Ketone-catalyzed asymmetric epoxidation reactions. Acc. Chem. Res. 2004 37 497-505. 

Chiral ketone-catalyzed asymmetric epoxidation of olefins 00S1979. 

Organocatalytic Oxidation. Ketone-Catalyzed Asymmetric Epoxidation of Alkenes and Synthetic Applications... 

The asymmetric epoxidation of alkenes constitutes a powerful approach to enantiomerically enriched epoxides, a class of highly versatile intermediates in organic synthesis [1]. Various effective epoxidation systems have been developed, including epoxidation of allylic [2, 3] and homoallylic [4] alcohols, metalunfunctionalized alkenes [5-7], and the nucleophilic epoxidation of electron-deficient alkenes [8]. During the past 10-15 years, much effort has been devoted to chiral ketone-catalyzed asymmetric epoxidation (Scheme 3.1). The subject has been described in great detail in the first edition [9] and other reviews [10]. This chapter provides an update on progress in this area since the first edition [9]. 

Warren JD, Shi Y. Chiral ketone-catalyzed asymmetric epoxidation of 2, 2-disubstituted vinylsilanes. J. Org. Chem. 1999 64(20) 7675-7677. 

Organocatalytic Oxidation. Ketone-catalyzed Asymmetric Epoxidation of Olefins... 

For recent reviews on chiral ketone catalyzed asymmetric epoxidation see ... 

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