Diastereoselective Epoxidation Of Allylically Substituted Alkenes Using Metalloporphyrin Catalysts

Abstract

Diastereoselective Epoxidation Of Allylically Substituted Alkenes Using Metalloporphyrins As Catalyst Provides High Trans-Selectivities (I.E., Trans-:Cis-Epoxide Ratio). A Diversity Of Cycloalkenes Bearing Different Allylic Substituents Are Shown To Be Efficiently Epoxidized To Afford The Corresponding Trans-Epoxides With Excellent Trans-Selectivities (Up To >98%) And Good Yields (Up To 99%). Acyclic Allylic Alkenes Bearing Different Allylic Substituents Are Efficiently Epoxidized To Afford The Corresponding Erythro-Epoxides With Good Erythro-Selectivities. The Metalloporphyrin-Catalyzed Reactions Exhibit Up To 20 Times Higher Trans-Selectivities Than The Conventional Method Using M-Chloroperoxybenzoic Acid As Oxidant.