Related Experiment Video
Updated: Jun 14, 2026

Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes
Published on: June 24, 2022
Resolution of the atropochiral biminap ligand and applications in asymmetric catalysis
Ibrahim Abdellah1, Nathalie Debono, Yves Canac
1CNRS, LCC (Laboratoire de Chimie de Coordination), 205, route de Narbonne, F-31077 Toulouse, France.
Abstract:
Enantiomeric resolution of the rac-biminap ligand is achieved through fractional crystallization of four diastereoisomeric palladium complexes involving ortho-metallated enantiomerically pure (R)-dimethyl(1-naphthylethyl)amine as a chiral auxiliary. After decomplexation, the absolute configuration of (R)-biminap and (S)-biminap has been unambiguously attributed by single-crystal X-ray crystallography, and their stereochemical purity is confirmed by measurement of their optical rotation and by re-derivatization with the initial resolving chiral complex. Palladium complexes of biminap are shown to efficiently catalyze Tsuji-Trost allylic substitution of 3-acetoxy-1,3-diphenylpropene by sodium dimethyl malonate. In the asymmetric version using the enantiomerically pure (R)-biminap ligand, significant solvent and anion effects are evident, and an ee up to 90% is obtained.
Related Concept Videos
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...
Prochirality
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.
Chirality at Nitrogen, Phosphorus, and Sulfur
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Chirality in Nature

