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

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