Design and synthesis of binaphthol-derived chiral ketone catalysts for dioxirane-mediated asymmetric epoxidation of olefins

Abstract

Binaphthol-derived chiral ketones 1a-c were synthesized and were shown to serve as active catalysts for asymmetric epoxidation of olefins using Oxone(R), although their enantioselectivities were not high. However, very interestingly, the stereochemical outcome of the resulting epoxides implicates that in the epoxidation using 1a-c, the planar transition state may be more favorable than the spiro transition state.