title: Chiral Lewis acid catalyzed resolution of racemic enol ester epoxides. Conversion of both enantiomers of an enol ester epoxide to the same enantiomer of acyloxy ketone.
abstract: This paper describes an efficient kinetic resolution of racemic enol ester epoxides via a chiral Lewis acid catalyzed rearrangement. Both enantiomerically enriched enol ester epoxides and alpha-acyloxy ketones can be obtained through this resolution. A positive nonlinear effect is observed in this process. By taking advantage of the mechanistic duality in acid-catalyzed enol ester epoxide rearrangement, we can completely convert a racemic enol ester epoxide into an enantiomerically enriched alpha-acyloxy ketone by treatment with a catalytic amount of a chiral Lewis acid followed by a catalytic amount of an achiral protic acid.
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
authors.forename: Xiaoming
authors.initials: X
authors.lastname: Feng
authors.forename: Lianhe
authors.initials: L
authors.lastname: Shu
authors.forename: Yian
authors.initials: Y
authors.lastname: Shi
mesh_terms: D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D002851:Chromatography, High Pressure Liquid; D004852:Epoxy Compounds / Q000138:chemical synthesis*; D004952:Esters / Q000737:chemistry; D006844:Hydrocarbons, Cyclic / Q000138:chemical synthesis*; D007659:Ketones / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D004852:Epoxy Compounds; D004952:Esters; D006844:Hydrocarbons, Cyclic; D007659:Ketones