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.
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.
Feng
Xiaoming
X
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
Shu
Lianhe
L
Shi
Yian
Y
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
D004852:Epoxy Compounds; D004952:Esters; D006844:Hydrocarbons, Cyclic; D007659:Ketones