Abstract
The renewed interest in electrosynthesis demonstrated by organic chemists in the last years has allowed for rapid development of new methodologies. In this review, advances in enantioselective electrosynthesis that rely on catalytic amounts of organic or metal-based chiral mediators are highlighted with focus on the most recent developments up to July 2020. Examples of C-H functionalization, alkene functionalization, carboxylation and cross-electrophile couplings are discussed, along with their related mechanistic aspects.
Highlights
The stereochemistry of organic compounds can dramatically influence their properties, such as biological activity of pharmaceuticals or macroscopic physical characteristics of polymers
The ability to control the stereochemical outcome in organic synthesis can be of great importance, and asymmetric catalysis is an indispensable tool in this endeavor
Outcould by the anode, mediated electrolysis is preferred direct oxidation can is lead to catalyst complex could be directly oxidizedinatsolution the anode, mediatedas electrolysis in solution preferred as direct adsorption on the electrode surface that may inhibit catalysis
Summary
The stereochemistry of organic compounds can dramatically influence their properties, such as biological activity of pharmaceuticals or macroscopic physical characteristics of polymers. As exemplified for a net-oxidative process, the electron transfer from a substrate to the anode can occur directly at the electrode surface (Figure 1a) or take place in solution with the aid of a homogeneous redox mediator. The latter represents indirect electrolysis (Figure 1b), where the mediator effectively acts as a catalyst for the electron transfer. In the context of asymmetric electrosynthesis, both redox mediators and catalysts can be chiral mediators and catalysts can be chiral and induce stereoselectivity in the reaction in which they are andused. Oxidative and reductive transformations and highlights recent developments up to July 2020
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