Enantioface-Differentiating Epoxidation of Alkylidenemalononitriles with Molecular Oxygen, catalyzed by Chiral Tertiary Amines

Abstract

The present paper describes the enantioface-differentiaing epoxidation of alkylidenemalononitriles with molecular oxygen, catalyzed by chiral tertiary amines. In the light of the by-product formation, the reaction path was concluded to involve intermolecular nucleophilic attack of a hydroperoxide intermediate catalyzed by a chiral tertiary amine. A similar epoxidation was demonstrated with cumylhydroperoxide in the presence of nicotine.