Related Experiment Video
Updated: Jun 7, 2026

Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction
Published on: August 23, 2018
Hydrogen-bond-mediated enantio- and regioselectivity in a Ru-catalyzed epoxidation reaction
Philipp Fackler1, Carola Berthold, Felix Voss
1Lehrstuhl für Organische Chemie I and Catalysis Research Center (CRC), Technische Universität München, Lichtenbergstr. 4, 85747 Garching, Germany.
Abstract:
A chiral epoxidation catalyst based on a tricyclic octahydro-1H-4,7-methanoisoindol-1-one scaffold, in which a hydrogen bonding site and the catalytically active ruthenium center are spatially separated, was synthesized. It was shown that epoxidation reactions in such a supramolecular catalyst occur with high enantio- and regioselectivity because the hydrogen bonds expose the substrate to the ruthenium porphyrin complex with a clear conformational preference. The epoxidation of 3-vinylquinolone proceeded in up to 95% ee (71% yield).
Related Concept Videos
Sharpless Epoxidation
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Radical Anti-Markovnikov Addition to Alkenes: Overview
Preparation of Epoxides
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...

