A pH Study on the Chiral Ketone Catalyzed Asymmetric Epoxidation of Hydroxyalkenes
The Journal of Organic Chemistry1998Vol. 63(9), pp. 3099–3104
Citations Over TimeTop 10% of 1998 papers
Abstract
A detailed study shows that the chiral ketone catalyzed asymmetric epoxidations of hydroxyalkenes are highly pH dependent. The lower enantioselectivity obtained at low pH is attributed to the substantial contribution of the direct epoxidation by Oxone. At high pH the epoxidation mediated by chiral ketone out-competes the racemic epoxidation, leading to higher enantioselectivity. The effective substrates include allylic alcohol, homoallylic alcohol, and bishomoallylic alcohol. In most cases, over 90% ee was obtained.
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