Lipase on carbon nanotube - An active, selective, stable and easy to optimize nanobiocatalyst for kinetic resolutions

An efficient nanobioconjugate of lipase B from Candida antarctica was prepared by the covalent binding on carboxy-functionalized single-walled carbon nanotubes and tested in batch and flow mode for the enzymatic...

Catalytic Atroposelective Dynamic Kinetic Resolutions and Kinetic Resolutions towards 3-arylquinolines via SNAr

Herein we report the catalytic atroposelective syntheses of pharmaceutically relevant 3-arylquinolines via the nucleophilic aromatic substitution (SNAr) of thiophenols into 3-aryl-2-fluoroquinolines mediated by catalytic amounts of Cinchona alkaloid-derived ureas. These...

Mutual kinetic resolution: probing enantiorecognition phenomena and screening for kinetic resolution with racemic reagents

This review highlights recent examples of mutual kinetic resolutions and describes how this approach can be used as a powerful tool to screen for efficient kinetic/parallel kinetic resolution protocols.

Isothiourea-Catalysed Sequential Kinetic Resolution of Acyclic (±)-1,2-Diols

The isothiourea-catalysed acylative kinetic resolution of a range of acyclic (±)-1,2-diols using 1 mol% of catalyst under operationally simple conditions is reported. Significantly, the bifunctional nature of (±)-1,2-diols was exploited in a sequential double kinetic resolution, in which both kinetic resolutions operate synergistically to provide access to highly enantioenriched products. The principles that underpin this process are discussed, and selectivity factors for the individual kinetic resolution steps are reported in a model system.

Allylic Chloro-Tetrahydropyridines: Kinetic Resolutions and Stereospecific Reactions of Enantiomerically Enriched Allyl Chlorides

We report the kinetic resolution of racemic allyl chlorides via a copper-catalysed asymmetric allylic alkylation. Novel 3-alkyl substituted tetrahydropyridines and enantioenriched 3-chloro-1,2,3,6-tetrahydropyridines are formed in high enantioselectivities. The piperidine-based allyl halides undergo highly enantiospecific substitution reactions with C, N, O and S-based nucleophiles. Experiments with deuterium-labelled chloro-tetrahydropyridine and DFT calculations were used to investigate the mechanistic pathways of the reactions.