Asymmetric Electrochemical Arylation in the Formal Synthesis of (+) Amurensinine

Asymmetric electrochemical synthesis has emerged as an attractive and sustainable alternative for the distinctive activation of bond connections in the preparation of diverse enantiomerically enriched targets, including natural products and pharmaceutical agents. Herein, we describe the chiral Lewis acid-catalyzed enantioselective electrochemical anodic coupling reaction as a key step in the presented formal synthesis of isopavine alkaloids. The direct functionalization of catechol derivatives with 2-acyl imidazoles was developed to provide a wide range of useful chiral alpha,alpha-diaryl carbonyl building blocks containing tertiary stereogenic centers with high reactivity and excellent stereoselectivity. The utility of this novel enantioselective electrochemical protocol is showcased by its implementation in the enantioselective formal synthesis of (+)-Amurensinine. [GRAPHICS] .

Automated summary

Asymmetric electrochemical synthesis is an attractive and sustainable method for preparing enantiomerically enriched targets like natural products and pharmaceutical agents. The chiral Lewis acid-catalyzed enantioselective electrochemical anodic coupling reaction is a key step in the formal synthesis of isopavine alkaloids. This method allows for unique activation of bond connections, resulting in the formation of diverse enantiomerically enriched targets.