Journal
CCS CHEMISTRY
Volume 3, Issue 12, Pages 338-347Publisher
CHINESE CHEMICAL SOC
DOI: 10.31635/ccschem.021.202000720
Keywords
asymmetric catalysis; electrochemistry; Lewis acid catalysis; arylation; alpha, alpha-diaryl carbonyl skeletons
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Funding
- National Natural Science Foundation of China [21702198, 21971227]
- Anhui Provincial Natural Science Foundation [1808085MB30]
- Fundamental Research Funds for the Central Universities [WK2340000090]
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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.
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] .
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